GB1584823A - 2-acylamino-5-chlorobenzenesulphonic acids useful as intermediates in the production of diazo components - Google Patents
2-acylamino-5-chlorobenzenesulphonic acids useful as intermediates in the production of diazo components Download PDFInfo
- Publication number
- GB1584823A GB1584823A GB3674377A GB3674377A GB1584823A GB 1584823 A GB1584823 A GB 1584823A GB 3674377 A GB3674377 A GB 3674377A GB 3674377 A GB3674377 A GB 3674377A GB 1584823 A GB1584823 A GB 1584823A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- group
- acid
- oxidation
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims abstract description 16
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000007513 acids Chemical class 0.000 title abstract description 3
- 239000000543 intermediate Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 22
- 230000003647 oxidation Effects 0.000 claims abstract description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- -1 2-chloro-5-acetamino-4-sulphoethylbenzene Chemical compound 0.000 claims description 18
- 238000005917 acylation reaction Methods 0.000 claims description 15
- 229910052783 alkali metal Inorganic materials 0.000 claims description 15
- 230000010933 acylation Effects 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 229960000583 acetic acid Drugs 0.000 claims description 12
- 239000012362 glacial acetic acid Substances 0.000 claims description 12
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- 150000001340 alkali metals Chemical group 0.000 claims description 11
- 230000000875 corresponding effect Effects 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000049 pigment Substances 0.000 claims description 8
- 230000020477 pH reduction Effects 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 229940099594 manganese dioxide Drugs 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 235000010755 mineral Nutrition 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 239000012736 aqueous medium Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000012286 potassium permanganate Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- JLWMMYZWEHHTFF-UHFFFAOYSA-N 2-[6-(3-carbamimidoylphenoxy)-4-[di(propan-2-yl)amino]-3,5-difluoropyridin-2-yl]oxy-5-(2-methylpropylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC(C(=O)NCC(C)C)=CC=C1OC1=NC(OC=2C=C(C=CC=2)C(N)=N)=C(F)C(N(C(C)C)C(C)C)=C1F JLWMMYZWEHHTFF-UHFFFAOYSA-N 0.000 claims description 2
- VEPOZWJTGLVFEU-UHFFFAOYSA-N 5-acetamido-2-chloro-4-sulfobenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=C(Cl)C=C1S(O)(=O)=O VEPOZWJTGLVFEU-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000004436 sodium atom Chemical group 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001117 sulphuric acid Substances 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000010626 work up procedure Methods 0.000 claims description 2
- 235000013350 formula milk Nutrition 0.000 claims 15
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- 241000237519 Bivalvia Species 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- 235000020639 clam Nutrition 0.000 claims 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- ZCGVPUAAMCMLTM-UHFFFAOYSA-N 2-amino-5-chlorobenzenesulfonic acid Chemical class NC1=CC=C(Cl)C=C1S(O)(=O)=O ZCGVPUAAMCMLTM-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 3
- VYZCFAPUHSSYCC-UHFFFAOYSA-N 2-amino-5-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1Cl VYZCFAPUHSSYCC-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- UPMIEBBZKWZYEZ-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1Cl UPMIEBBZKWZYEZ-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
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/51—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762639668 DE2639668A1 (de) | 1976-09-03 | 1976-09-03 | 2-acylamino-5-chlor-benzolsulfonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1584823A true GB1584823A (en) | 1981-02-18 |
Family
ID=5987047
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3674377A Expired GB1584823A (en) | 1976-09-03 | 1977-09-02 | 2-acylamino-5-chlorobenzenesulphonic acids useful as intermediates in the production of diazo components |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS5331644A (enrdf_load_stackoverflow) |
| CH (1) | CH632242A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2639668A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2363548A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1584823A (enrdf_load_stackoverflow) |
| IT (1) | IT1085035B (enrdf_load_stackoverflow) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1436059A (en) * | 1974-04-18 | 1976-05-19 | Ici Ltd | 2-amino-4,5-disulphobenzoic acid and derivatives |
-
1976
- 1976-09-03 DE DE19762639668 patent/DE2639668A1/de not_active Withdrawn
-
1977
- 1977-08-31 CH CH1062377A patent/CH632242A5/de not_active IP Right Cessation
- 1977-09-01 IT IT2719177A patent/IT1085035B/it active
- 1977-09-02 GB GB3674377A patent/GB1584823A/en not_active Expired
- 1977-09-02 JP JP10504977A patent/JPS5331644A/ja active Pending
- 1977-09-05 FR FR7726813A patent/FR2363548A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2639668A1 (de) | 1978-03-09 |
| IT1085035B (it) | 1985-05-28 |
| JPS5331644A (en) | 1978-03-25 |
| FR2363548B1 (enrdf_load_stackoverflow) | 1981-06-12 |
| CH632242A5 (en) | 1982-09-30 |
| FR2363548A1 (fr) | 1978-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0303291B1 (en) | Fluorinated benzoyl compounds | |
| US4750978A (en) | Method for oxidizing groups to carboxylic acids under basic conditions | |
| GB1584823A (en) | 2-acylamino-5-chlorobenzenesulphonic acids useful as intermediates in the production of diazo components | |
| US2877220A (en) | Method of preparing lysine | |
| EP0245835B1 (en) | Novel thiophene derivatives and methods for producing the same | |
| US3514471A (en) | Process for the manufacture of 3-phenyl or substituted phenyl-7-amino-cumarins | |
| US4182880A (en) | 1,8-Naphthyridine compounds and process for preparing the same | |
| US4521616A (en) | Method for the preparation of fluoroanthranilic acids | |
| US5453512A (en) | Method of producing 2-amino-3-nitro-5-halogenopyridine | |
| JPH04211072A (ja) | ２−アルキルチオ−１，３，４−チアジアゾール類の製造方法 | |
| KR950001026B1 (ko) | 페니실란산 유도체의 개선된 제조방법 | |
| IL26949A (en) | 3-nitro-4-halophenol derivatives and their preparation | |
| US4892950A (en) | Process for the preparation of naphthalene-1,8-dicarboximides | |
| JPS6228797B2 (enrdf_load_stackoverflow) | ||
| US4939262A (en) | 6-ethyl-3-amino or nitro-2,4-dihalogenopyridine compounds | |
| GB2159154A (en) | Methyl 2-(2-hydroperoxy-2-propyl)naphthalene-6-carboxylate | |
| US2649482A (en) | Method for the preparation of 4-chloro-2, 5-dialkoxyanilines | |
| US5808014A (en) | Process for the preparation of arlazotetronic acid derivatives | |
| US3749719A (en) | Process for amino-s-triazolo-(4,3-a)pyrazines | |
| US3238210A (en) | Manufacture of a thiachromonoacridone-containing pigment | |
| JPH0128013B2 (enrdf_load_stackoverflow) | ||
| CA1120493A (en) | Process for producing 4'-(2-carboxy-ethyl)phenyl trans-4-aminomethylcyclohexanecarboxylate or the acid-addition salts thereof and intermediates for producing the same | |
| US6084134A (en) | Process for preparing 9-anthracenecarbaldehyes | |
| US4009176A (en) | Conversion of 2-aminonaphtho[1,2 d] selenazole to 2-methylnaphtho[1,2 d] selenazole | |
| NL8800803A (nl) | Werkwijze voor de bereiding van zuivere 1-fenyl-3-carbalkyloxy-5-hydroxypyrazolen. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |