CS199233B2 - Method of preparing 2-sulphomethyl-6-hydroxy-2-pyridones - Google Patents
Method of preparing 2-sulphomethyl-6-hydroxy-2-pyridones Download PDFInfo
- Publication number
- CS199233B2 CS199233B2 CS891371A CS891371A CS199233B2 CS 199233 B2 CS199233 B2 CS 199233B2 CS 891371 A CS891371 A CS 891371A CS 891371 A CS891371 A CS 891371A CS 199233 B2 CS199233 B2 CS 199233B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydroxy
- formula
- pyridone
- alkyl
- methyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 6
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical class OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 claims abstract 6
- 150000001875 compounds Chemical class 0.000 claims description 25
- -1 methoxyphenyl Chemical group 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000005521 carbonamide group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 claims 8
- GSIGQQKMRKAPLD-UHFFFAOYSA-N (2-hydroxy-6-oxo-1h-pyridin-3-yl)methanesulfonic acid Chemical class OC1=CC=C(CS(O)(=O)=O)C(=O)N1 GSIGQQKMRKAPLD-UHFFFAOYSA-N 0.000 claims 1
- RWBLSVPYDPODTR-UHFFFAOYSA-N 1-ethyl-6-hydroxy-4-methylpyridin-2-one Chemical compound CCN1C(O)=CC(C)=CC1=O RWBLSVPYDPODTR-UHFFFAOYSA-N 0.000 claims 1
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 claims 1
- IVEOCYLKEXGIPE-UHFFFAOYSA-N CCN1C(O)=CC(C)=C(C(N)=O)C1=O Chemical compound CCN1C(O)=CC(C)=C(C(N)=O)C1=O IVEOCYLKEXGIPE-UHFFFAOYSA-N 0.000 claims 1
- OWMJAQBUFVTERI-UHFFFAOYSA-N n-(2-formylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1C=O OWMJAQBUFVTERI-UHFFFAOYSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 27
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000975 dye Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 2
- MRXZEDMLQMDMGB-UHFFFAOYSA-N 3-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(C=O)=C1 MRXZEDMLQMDMGB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 235000010265 sodium sulphite Nutrition 0.000 description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- LQPYDXCUTLDVQX-UHFFFAOYSA-N 2-chlorobenzaldehyde 6-hydroxy-4-methyl-1H-pyridin-2-one Chemical compound CC1=CC(O)=NC(O)=C1.ClC1=CC=CC=C1C=O LQPYDXCUTLDVQX-UHFFFAOYSA-N 0.000 description 1
- SHHKMWMIKILKQW-UHFFFAOYSA-N 2-formylbenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=O SHHKMWMIKILKQW-UHFFFAOYSA-N 0.000 description 1
- OTEBTSPEXWSPLD-UHFFFAOYSA-N 2-hydroxy-4-methyl-6-oxo-1h-pyridine-3-carboxamide Chemical compound CC1=CC(=O)NC(O)=C1C(N)=O OTEBTSPEXWSPLD-UHFFFAOYSA-N 0.000 description 1
- SIXYIEWSUKAOEN-UHFFFAOYSA-N 3-aminobenzaldehyde Chemical compound NC1=CC=CC(C=O)=C1 SIXYIEWSUKAOEN-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical compound CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- VURKZGVVEBTDFJ-UHFFFAOYSA-N acetaldehyde 6-hydroxy-4-phenyl-1H-pyridin-2-one Chemical compound C(C)=O.OC1=NC(=CC(=C1)C1=CC=CC=C1)O VURKZGVVEBTDFJ-UHFFFAOYSA-N 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- KBKWZUVMKBNTFP-UHFFFAOYSA-N n-(3-formylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C=O)=C1 KBKWZUVMKBNTFP-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- QJQRNDGUWQVAEV-AAFSJPGBSA-M sodium bisulfite adduct Chemical compound [Na+].[O-]S(=O)(=O)C([C@H]1N(C(C2=C3)=O)C=C(C1)/C=C/C(=O)N(C)C)NC2=CC1=C3OCO1 QJQRNDGUWQVAEV-AAFSJPGBSA-M 0.000 description 1
- VYKVQJFOZDGJLN-UHFFFAOYSA-M sodium hydrogen sulfite sulfurous acid Chemical compound [Na+].OS(O)=O.OS([O-])=O VYKVQJFOZDGJLN-UHFFFAOYSA-M 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B45/00—Complex metal compounds of azo dyes
- C09B45/02—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups
- C09B45/025—Preparation from dyes containing in o-position a hydroxy group and in o'-position hydroxy, alkoxy, carboxyl, amino or keto groups of azo-pyridone series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/0067—Azodyes with heterocyclic compound as coupling component
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/008—Monoazo dyes
- C09B62/0088—Monoazo dyes with heterocyclic compound as coupling component
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
Description
R atom vodíku, alkylovou skupinu s 1 až 4 atomy uhlíku, halogenalkylovou, hydroxyalkylovou, aminoalkylovou, acetylaminoalkylovou nebo fenylalkylovou skupinu vždy s 1 až 4 atomy uhlíku v alkylovém podíle, fenylovou skupinu, methylfénylovou skupinu nebo methoxyfenylovou skupinu,R is hydrogen, C1-C4alkyl, haloalkyl, hydroxyalkyl, aminoalkyl, acetylaminoalkyl or phenylalkyl having 1 to 4 carbon atoms in the alkyl moiety, phenyl, methylphenyl or methoxyphenyl,
R‘ atom vodíku, alkylovou skupinu s 1 až atomy uhlíku nebo fenylovou skupinu,R @ 1 is hydrogen, C1 -C6 alkyl or phenyl,
Z atom vodíku, karbonamidovou skupinu, kyanovou skupinu nebo skupinu estery kraboxylové kyseliny obecného vzorce kde R“ znamená alkylovou skupinu s 1 až 4 atomy uhlíku,Z is a hydrogen atom, a carbonamide group, a cyano group or a carboxylic acid ester group of the general formula: wherein R 'represents an alkyl group having 1 to 4 carbon atoms,
Y atom vodíku, alkylovou skupinu s 1 až 4 atomy uhlíku, skupinu fenylovou, sulfofenylovou, acetylaminofenylovou, nitrofenylovou, halogenfenylovou, methoxyfenylovou, amlnofenylovou, formyifenylovou, thienylovou, pyridylovou nebo furylovou skupinu.Y is hydrogen, C1-C4alkyl, phenyl, sulfophenyl, acetylaminophenyl, nitrophenyl, halophenyl, methoxyphenyl, amnophenyl, formyiphenyl, thienyl, pyridyl or furyl.
Vhodnými jsou sloučeniny obecného vzorce 1, ve kterých znamená Y atom vodíku nebo fenylovou skupinu, zvláště aminofenylovou nebo acetylfenylovou skupinu, jestliže znamená Y aminofenylovou skupinu, může být aminofenylová skupina popřípadě dodatečně acylována. Důležité jsou takové sloučeniny, které obsahují jako Y acylaminofenylovou skupinu, kde je acylová skupina reaktivní s vláknem. Jakožto acylové skupiny reaktivní s vláknem přicházejí v úvahu zvláště halogentriazinóvé skupiny, popřípadě jakožto acylační prostředky halogentriaziny. Důležité sloučeniny reaktivní s vláknem, připravené způsobem podle vynálezu, jsou tudíž například sloučeniny obecného vzorce 1, kde znamená Y 3-(dichlór-l,3,5-triazinylamino) skupinu nebo 4-(dichlor-1,3,5-triazinyl'amino skupinu, popřípadě odpovídající monochlorazinoskupinu, která má na triazinovém jádru místo druhého atomuCompounds of formula (I) in which Y represents a hydrogen atom or a phenyl group, in particular an aminophenyl or acetylphenyl group, when Y represents an aminophenyl group, may optionally be additionally acylated. Of note are those compounds which contain, as Y, an acylaminophenyl group wherein the acyl group is reactive with the fiber. Possible fiber-reactive acyl groups are, in particular, halonriazine groups, optionally as halosriazine acylating agents. Thus, important reactive fiber-reactive compounds prepared by the process of the invention are, for example, compounds of formula 1 wherein Y is 3- (dichloro-1,3,5-triazinylamino) or 4- (dichloro-1,3,5-triazinyl). an amino group, optionally corresponding to a monochlorazino group, having a second atom on the triazine nucleus
R“OOC—R “OOC”
9 233 aminoskupinu, alkoholovou, · fenovou nebo merkaptonovou skupinu.933 amino, alcohol, phenol or mercapto group.
Sulf oalkyl-6-hydroxy-2-pyridony · mohou být ve více tautomerních formách. Pro zjednodušení se vzorce uvádějí vždy jen v jedné tautomerní formě, výslovně se však· zdůrazňuje, že se vždy jak v popise, tak zvláště v definici předmětu vynálezu míní jakákoliv tautomerní forma.Sulfoalkyl-6-hydroxy-2-pyridones may be in multiple tautomeric forms. For the sake of simplicity, the formulas are given in only one tautomeric form, but it is expressly emphasized that in the description and particularly in the definition of the subject matter any tautomeric form is meant.
Pyridonem se myslí rovněž příslušné na atomu dusíku pyrídonového jádra atomem vodíku substituované sloučeniny, jakož také • odpovídající tautomerní · 2,6-dihydrorypyrydiny.Pyridone is also meant to refer to the corresponding nitrogen atom of the pyridine nucleus of the hydrogen-substituted compound as well as the corresponding tautomeric 2,6-dihydrorypyrydines.
Významnou skupinou sloučenin připravených způsobem podle vynálezu jsou sloučeniny obecného vzorce 1, ve kterých R a R* znamenají vždy atomy vodíku nebo alkylové skupiny · nejvýše se 4 atomy uhlíku, zvláště methylovou nebo ethylovou skupinu, a Y znamená atom vodíku.An important group of compounds prepared by the process according to the invention are those compounds of the formula I in which R and R * are each hydrogen or alkyl groups of up to 4 carbon atoms, in particular methyl or ethyl, and Y is hydrogen.
Jinou významnou skupinou sloučenin připravených · způsobem podle vynálezu jsou sloučeniny obecného vzorce 1, ve kterých znamená Y atom vodíku, R‘ alkylovou skupinu s 1 až 4 atomy uhlíku nebo fenylovou skupinu, methylfenylovou skupinu nebo methoxyfenylovou. skupinu a R aminoalkylovou skupinu s 1 až ·4 atomy uhlíku; tyto sloučeniny mají význam pro přípravu barviv.Another important group of compounds prepared by the process of the invention are those compounds of formula (I) wherein Y is hydrogen, R 1 -C 4 alkyl or phenyl, methylphenyl or methoxyphenyl. and R is C 1 -C 4 aminoalkyl; these compounds are important for the preparation of dyes.
Z · těchto sloučenin mají . opět . obzvláštní význam sloučeniny, kde R‘ · znamená alkylovou skupinu s 1 až 4 atomy uhlíku, zvláště methylovou skupinu.These compounds have. again. in particular, the meaning of a compound in which R‘ represents an alkyl group having 1 to 4 carbon atoms, in particular a methyl group.
3-Sulfoalkyl-6-hydrox2-2-pyridony obecného vzorce 1 se způsobem podle vynálezu připravují tak, že se nechá · reagovat v polo-The 3-sulfoalkyl-6-hydroxy-2-pyridones of the formula I are prepared by the process according to the invention by reacting in a semi-
kde R, · R‘ a Z mají · význam uvedený u ' obecného vzorce lr s · bisulfitovými adičními · sloučeninami aldehydů obecného vzorce 3,wherein R, R R and Z are as defined in formula (1r) with bisulfite addition compounds of aldehydes of formula (3),
(3/ roztoku a při teplotě místnosti nébo · při zvýšené teplotě. Bísulfitové · adiční · sloučeniny aldehydů, kterých se používá pro· reakci s · 6-hydrory-2-pyridony, se s výhodou připravují předem. Může se jich však použít také tak, že se vytvářejí teprve v průběhu reakce s 6-hydrory-2-pyridony. · K tomu může docházet zvláště postupným přidáváním aldehydu do vodné ,směsl pyridonu s kyselým siřičitanem sodným nebo draselným. Jestliže · v óbecném vzorci 2 znamená Z kyanoskupinu, skupinu esteru karboxylové kyseliny · nebo karbonamidovou skupinu, může se tato skupina po · zavedení sulfoalkylové skupiny odštěpit zmýdelněním.(3) solution and at room temperature or elevated temperature. The bisulfite addition compounds of the aldehydes used for the reaction with the 6-hydrory-2-pyridones are preferably prepared in advance. This may occur, in particular, by the gradual addition of an aldehyde to an aqueous mixture of pyridone with sodium or potassium bisulphite. % carboxylic acid or carbonamide group, this group can be cleaved by saponification after the sulfoalkyl group has been introduced.
Sloučeniny připravené způsobem podle vynálezu jsou nové. Jsou vhodné jakožto výchozí látky · pro přípravu barviv. Tak' · · lze zvláště kopulovat snadno sloučeniny obecného vzorce 1 s dlazosložkami na barviva obecného vzorce 4,The compounds prepared by the process of the invention are novel. They are suitable as starting materials for the preparation of dyes. Thus, in particular, the compounds of the formula 1 can be coupled easily with the dye components for the colorants of the formula 4,
kde R, R‘ a ·Υ mají shora uvedený význam a D znamená zbytek diazosložky, zvláště díazosložky benzenové nebo naftalenové řady.wherein R, R ‘and · Υ are as defined above and D represents the remainder of the diazo component, especially the diazo component of the benzene or naphthalene series.
Obzvláštní význam · mají barviva · obecného vzorce · (4), která obsahují skupinu způsobující rozpustnost · ve ’ vodě například skupinu sulfonové kyseliny a kromě · toho reaktivní skupinu, popřípadě volnou acylovatelnou aminoskupinu buď v diazosložce, nebo v pyridonové kopulační složce, takže lze · barviva obecného vzorce 4, popřípadě 3-sulfoalkyl-6-hydrory-2-pyridonové výchozí· sloučeniny, jako například sloučeniny obecného vzorce 2, acylací halogenidem nebo anhydridem a- . cylové · sloučeniny obsahující reaktivní zbytek převést na -sloučeniny reaktivní s vláknem.Of particular interest are the dyes of the formula (4) which contain a water-solubility group, for example a sulfonic acid group and, in addition, a reactive group or a free acylated amino group either in the diazo component or in the pyridone coupling component. dyes of formula (4) and optionally 3-sulfoalkyl-6-hydrory-2-pyridone starting compounds such as compounds of formula (2) by acylation with a halide or α-anhydride. the cylindrical compounds containing the reactive moiety can be converted to fiber reactive compounds.
Jakožto reaktivní zbytek přichází · v úvahu zvláště halogen-l,3,5-thiazinová skupina.As the reactive moiety, a halogen-1,3,5-thiazine group is particularly suitable.
Barviva obecného . vzorce 4 . se vyznačují vysokou intenzitou barvy. Vybarvení · těmito barvivý se vyznačují brilantními, čistými . odstíny dobré stálosti.Dyes. of formula 4. are characterized by high color intensity. Coloring · These dyes are characterized by brilliant, clean. shades of good stability.
Zavádění skupiny sulfonové kyseliny · do pyridonu obecného vzorce · 2 způsobem podle vynálezu má tu výhodu, že v azosloučeninách rozpustných ve vodě, které obsahují jakožto kopulační složku 1,3,4-trisubstituovaný-6-hydrory-2-pyridon · kromě skupiny způsobující rozpustnost ve vodě vázané v diazosložce, je skupina způsobující rozpustnost ve vodě vázána také v kopulační složce. To vede k· lepší vypíratelnosti na vlákně nefirovaných podílů takových barviv, · jakož kde Y má shora uvedený význam a · Me je atom alkalického kovu, například ve vodnémThe introduction of the sulfonic acid group into the pyridone of formula (2) by the process according to the invention has the advantage that in water-soluble azo compounds which contain 1,3,4-trisubstituted-6-hydrory-2-pyridone as coupling component in addition to the solubility group in the water bound in the diazo component, the water solubility group is also bound in the coupling component. This leads to · better washability on the fiber-free portions of such dyes, as · where Y is as defined above and · Me is an alkali metal atom, e.g.
6 také ke zlepšení tiskových past, které se připravují za použití těchto barviv.6 also improve printing pastes that are prepared using these dyes.
V následujících příkladech jsou díly a procenta, pokud není jinak uvedeno, míněny hmotnostně a teploty se uvádějí ve °C. Mezi hmotnostními a objemovými díly je stejný poměr jako mezi g a cm3.In the following examples, parts and percentages are by weight unless otherwise indicated, and temperatures are given in ° C. There is the same ratio between parts by weight and volume as between g and cm 3 .
PřikladlHe did
153 dílů l-ethyl-4-methyl-6-hydroxypyridon-2-u se rozpustí v 1500 dílech vody za přísady 100 dílů 40% sodného louhu při hodnotě pH 8. Do tohoto roztoku se vkapává při teplotě 30 až 35 °C v průběhu 15 minut vodný roztok adiční sloučeniny kyselého siřičitanu sodného a formaldehydu, připravené smíšením 260 dílů 40% roztoku kyselého siřičitanu sodného a 81 dílu 37% formaldehydového roztoku. Mírně exotermní reakcí stoupne teplota na 55 QC. Míchá se ještě po dobu jedné hodiny při této teplotě. Chromatografií v tenké vrstvě lze dokázat pouze ještě malé množství výchozí látky. Roztok se pak okyselí 110 objemovými díly 36% kyseliny solné a ochladí se na 5 °C. Za jednu hodinu se odfiltruje malé množství vykrystalisované výchozí látky. Zbylý roztok, jehož obsah l-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyridon-2-u se stanoví titrací roztokem diazotovaného anilinu, se může přímo použít pro kopulaci.153 parts of 1-ethyl-4-methyl-6-hydroxypyridone-2-ol are dissolved in 1500 parts of water with the addition of 100 parts of 40% sodium hydroxide solution at pH 8. This solution is added dropwise at 30 to 35 ° C during 15 minutes aqueous solution of sodium bisulfite adduct and formaldehyde prepared by mixing 260 parts of a 40% sodium sulfite solution and 81 parts of a 37% formaldehyde solution. A slightly exothermic reaction raised the temperature to 55 Q C. Stirring is continued for one hour at this temperature. Only a small amount of starting material can be detected by thin layer chromatography. The solution was then acidified with 110 volumes of 36% hydrochloric acid and cooled to 5 ° C. After one hour, a small amount of crystallized starting material was filtered off. The remaining solution, whose content of 1-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyridone-2-u is determined by titration with a solution of diazotized aniline, can be used directly for coupling.
Jestliže se použije místo l-ethyl-4-methyl-6-hydroxypyridon-2-u l-fenyl-4-methyl-6-hydroxypyridon-2-u, l,4-dlmethyl-6-hydroxypyridon-2-u nebo 2,6-dihydroxy-4-methylpyridinu, získají se způsobem uvedeným v tomto příkladu rovněž odpovídají sloučeniny obsahující sulfomethylové skupiny.When 1-ethyl-4-methyl-6-hydroxypyridone-2-u is used instead of 1-phenyl-4-methyl-6-hydroxypyridon-2-u, 1,4-dimethyl-6-hydroxypyridone-2 or u 6-dihydroxy-4-methylpyridine, sulfomethyl-containing compounds are also obtained as described in this example.
Příklad 2Example 2
К neutralizovanému roztoku 17,3 dílu 1-aminobenzen-3-sulfonové kyseliny ve 100 dílech vody a 100 dílech ledu se nalije roztok 18,5 dílu kyanurchloridu v 50 dílech acetonu a v průběhu kondensace se prikapáváním 2N sodného louhu udržuje hodnota pH 6 až 7. Po ukončené kondenšaci se přidá neutrální roztok l,3-diaminobenzen-4-sulfonové kyseliny, zahřeje se na 20 až 25 °C a hodnota pH roztoku se udržuje přikapáváním 2N sodného louhu na 6 až 7. Jakmile nelze ve směsi již dokázat žádnou diaminobenzensulfonovou kyselinu, přidá se 7 dílů dusitanu sodného a po rozpuštění se nalije na směs 200 dílů ledu a 25 dílů koncentrované kyseliny solné. Žlutá suspense diazosloučeniny se míchá po dobu jedné hodiny v ledové lázni a pak se rozruší malý nadbytek dusité kyseliny přidáním sulfamínové kyseliny. Do této diazosuspense se nyní nalije roztok 24,7 dílu l-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyridon-2-u ve 160 dílech vody. Hodnota pH, která je zpočátku 1,5, se přikapáváním sodného louhu zvýší na 3,5, přičemž se získá čirý žlutý roztok. Míchá se ještě po dobu jedné hodiny při hodnotě pHTo a neutralized solution of 17.3 parts of 1-aminobenzene-3-sulfonic acid in 100 parts of water and 100 parts of ice, a solution of 18.5 parts of cyanuric chloride in 50 parts of acetone is poured, maintaining the pH of 6-7 during dropping. After the condensation is completed, a neutral solution of 1,3-diaminobenzene-4-sulfonic acid is added, warmed to 20-25 ° C and the pH of the solution is maintained at 6 to 7 by dropwise addition of 2N sodium hydroxide solution. 7 parts of sodium nitrite are added and after dissolution is poured onto a mixture of 200 parts of ice and 25 parts of concentrated hydrochloric acid. The yellow diazo compound suspension is stirred for 1 hour in an ice bath, and then a small excess of nitrous acid is destroyed by the addition of sulfamic acid. A solution of 24.7 parts of 1-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyridone-2 in 160 parts of water is now poured into this diazosuspension. The pH, which is initially 1.5, is increased to 3.5 by dropwise addition of sodium hydroxide solution, giving a clear yellow solution. Stir for one hour at pH
3,5 v ledové lázni, hodnota pH se pak upraví na 7 a barvivo se vysráží přidáním chloridu draselného. Tak získané barvivo vybarvuje bavlnu na čisté žluté odstíny s nádechem do zelena.3.5 in an ice bath, the pH is then adjusted to 7 and the dye is precipitated by the addition of potassium chloride. The dye thus obtained dyes cotton to pure yellow shades with a green tint.
P ř í к 1 a d 3Example 1 a d 3
19,6 dílu l-ethyl-3-aminokarbonyl-4-methyl-6-hydroxypyridon-2-u se rozpustí v 50 dílech vody za přísady sodného louhu při hodnotě pH 7. Do tohoto roztoku se přidá roztok adiční sloučeniny formaldehydu a kyselého siřičitanu sodného, připravený smíšením 8,1 dílu 37% formaldehydového roztoku a 26 dílů 40% roztoku kyselého siřičitanu sodného. Míchá se po dobu jedné hodiny při teplotě 80 až 85 °C, až již v reakční směsi nelze dokázat výchozí látky chromatografií v tenké vrstvě. Nechá se zchladnout a přidáním 10 ml 32% kyseliny solné se reakce upraví na výrazně kongokyselou. Přidáním 20 dílů chloridu draselného vypadne vzniklý l-ethyl-3^sulfomethyl-4-methyl-5-aminokarbonyl-6-hydroxypyridon-2. Zmýdelněním aminokarbonylové skupiny jednohodinovým varem ve 100 dílech 2N sodného louhu se získá l-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyridon-2, který je totožný s produktem popsaným v příkladu 1, odstavec 1.19.6 parts of 1-ethyl-3-aminocarbonyl-4-methyl-6-hydroxypyridone-2 are dissolved in 50 parts of water with sodium hydroxide solution at pH 7. To this solution is added a solution of formaldehyde addition compound and acid sulfite Sodium sulfite solution was prepared by mixing 8.1 parts of a 37% formaldehyde solution and 26 parts of a 40% sodium sulfite solution. Stir for one hour at 80-85 ° C until the starting material can no longer be detected by thin layer chromatography. Allow to cool and add 10 ml of 32% hydrochloric acid to make the reaction considerably congoic. Addition of 20 parts of potassium chloride precipitates the resulting 1-ethyl-3-sulfomethyl-4-methyl-5-aminocarbonyl-6-hydroxypyridone-2. The saponification of the aminocarbonyl group by boiling in 100 parts of 2N sodium hydroxide solution for one hour gives 1-ethyl-3-sulfomethyl-4-methyl-6-hydroxypyridone-2, which is identical to the product described in Example 1, paragraph 1.
Jestliže se použije místo l-ethyl-3-aminokarbonyl-4-methyl-6-hydroxypyridon-2-u ekvivalentního množství l-fenyl-3-aminokarbonyl-4-methyl-6-hydroxypyridon-2-u, 1,4-dimethyl-3-amínokarbonyl-6-hydroxypyridon-2-u, 2,6-dihydroxy-3-aminokarbonyl-4-methylpyridinu nebo l-butyl-4-fenyl-3-aminokarbonyl-6-hydroxypyridon-2-u, získají se způsobem popsaným v tomto příkladu rovněž odpovídající sloučeniny obsahující sulfomethylové skupiny.When an equivalent amount of 1-phenyl-3-aminocarbonyl-4-methyl-6-hydroxypyridone-2-u, 1,4-dimethyl is used in place of 1-ethyl-3-aminocarbonyl-4-methyl-6-hydroxypyridone-2-u 3-Aminocarbonyl-6-hydroxypyridon-2-one, 2,6-dihydroxy-3-aminocarbonyl-4-methylpyridine or 1-butyl-4-phenyl-3-aminocarbonyl-6-hydroxypyridone-2-one, obtained by described in this example also corresponding compounds containing sulfomethyl groups.
PřikládáHe attaches
Nejdříve se postupuje způsobem popsaným ' v příkladu 2. Po ukončené diazotaci se hodnota pH diazotační směsi nastaví přidáním 20 dílů bezvodého uhličitanu sodného na 9 a přidá se roztok 29 dílů l-ethyl-3-sulfomethyl-4-methyl-5-aminokarbonyl-6-hydroxypyrodin-2-u ve 160 dílech vody. Po dvouhodinovém míchání při teplotě 10 °C a při hodnotě pH roztoku asi 9 je kopulace ukončena za současného odštěpení aminokarbonylové skupiny. Ze žlutého roztoku vypadne barvivo přidáním chloridu draselného. Je totožné s barvivém připraveným způsobem popsaným v příkladu 2.The pH of the diazotization mixture is adjusted to 9 by adding 20 parts of anhydrous sodium carbonate and a solution of 29 parts of 1-ethyl-3-sulfomethyl-4-methyl-5-aminocarbonyl-6 is added. -hydroxypyrodine-2 in 160 parts water. After stirring at 10 ° C for 2 hours and at a pH of about 9, the coupling is terminated while cleavage of the aminocarbonyl group. The dye precipitates from the yellow solution by the addition of potassium chloride. It is identical to the dye prepared as described in Example 2.
P ř í к 1 ad 5Example 1
Do směsi 260 dílů 40% roztoku kyselého siřičitanu sodného a 260 dílů ledu v inertním prostředí se přikapává po dobu asi 15 minut 44 dílů acetaldehydu a míchá se tak dlouho, až zanikne formaldehydový zápach. Vzniklý roztok se nalije do roztoku 169 dílů l-(/3-hydroxyethyl)-4-methyl-6-hydroxypyridon-2-u v 500 dílech vody a 100 dílech 40% sodného louhu a míchá se po dobu dvou hodin při teplotě 50 až 55 °C. Pak se ochladí na teplotu místnosti, reakce se prikapáváním koncentrované kyseliny solné upraví na výrazně kongokyselou a smíchá se se 100 díly chloridu draselného. Po míchání přes noc vyloučený l-(/3-hydroxyethyl]-3-(.a-sulfoethyl)-4-methy l-6-hydroxypyridon-2- se odfiltruje a usuší.To a mixture of 260 parts of a 40% sodium bisulfite solution and 260 parts of ice in an inert medium was added dropwise 44 parts of acetaldehyde for about 15 minutes and stirred until the formaldehyde odor ceased. The resulting solution was poured into a solution of 169 parts of 1- (3-hydroxyethyl) -4-methyl-6-hydroxypyridone-2-uv in 500 parts of water and 100 parts of 40% sodium hydroxide solution and stirred for two hours at 50-55 ° C. Deň: 32 ° C. It is then cooled to room temperature, the reaction is made dropwise with concentrated hydrochloric acid to a significantly congoic acid and mixed with 100 parts of potassium chloride. After stirring overnight, the precipitated 1- (β-hydroxyethyl) -3- (α-sulfoethyl) -4-methyl-6-hydroxypyridone-2- is filtered off and dried.
Další pyridony substituované v poloze 3 sulfoalkylovou skupinou se získají reakcí ve sloupci II následující tabulky uvedeného pyridonu s bisulfltovými adičními sloučeninami aldehydů uvedených ve sloupci III způsobem popsaným v tomto příkladu.Additional pyridones substituted at the 3-position with a sulfoalkyl group are obtained by reaction in column II of the following table of said pyridone with the bisulfite addition compounds of the aldehydes listed in column III as described in this example.
Jestliže se kondensuje způsobem popsaným v příkladu 2 kyanurchlorid s amoniakem a pak s l,3-diaminobenzen-4-sulfonovou kyselinou, získaný produkt se diazotuje a pak se kopuluje s pyridonem číslo 14, získá se dobře ve vodě rozpustné žluté reaktivní barvivo.When condensed as described in Example 2 with ammonia and then 1,3-diaminobenzene-4-sulfonic acid, the product obtained is diazotized and then coupled with pyridone # 14 to give a well water soluble yellow reactive dye.
Claims (9)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1705671A CH572470A5 (en) | 1971-11-23 | 1971-11-23 | 3-sulphoalkyl-6-hydroxypyrid-2-ones - coupling components for prepn of dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199233B2 true CS199233B2 (en) | 1980-07-31 |
Family
ID=4422411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS891371A CS199233B2 (en) | 1971-11-23 | 1971-12-22 | Method of preparing 2-sulphomethyl-6-hydroxy-2-pyridones |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH572470A5 (en) |
| CS (1) | CS199233B2 (en) |
| PL (1) | PL88949B1 (en) |
-
1971
- 1971-11-23 CH CH1705671A patent/CH572470A5/en not_active IP Right Cessation
- 1971-12-20 PL PL15231371A patent/PL88949B1/pl unknown
- 1971-12-22 CS CS891371A patent/CS199233B2/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL88949B1 (en) | 1976-10-30 |
| CH572470A5 (en) | 1976-02-13 |
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