DE2037295A1 - Verfahren zur Herstellung von Paraban saurederivaten - Google Patents
Verfahren zur Herstellung von Paraban saurederivatenInfo
- Publication number
- DE2037295A1 DE2037295A1 DE19702037295 DE2037295A DE2037295A1 DE 2037295 A1 DE2037295 A1 DE 2037295A1 DE 19702037295 DE19702037295 DE 19702037295 DE 2037295 A DE2037295 A DE 2037295A DE 2037295 A1 DE2037295 A1 DE 2037295A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- optionally substituted
- thio
- parabanic acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical class O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 title description 14
- -1 arylene radical Chemical class 0.000 claims description 13
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- RZRWPZCVCSHROS-UHFFFAOYSA-N cyanatoselanylsulfanyl cyanate Chemical compound S([Se]OC#N)OC#N RZRWPZCVCSHROS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910001867 inorganic solvent Inorganic materials 0.000 claims description 3
- 239000003049 inorganic solvent Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910001412 inorganic anion Inorganic materials 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- LTPCOIDSGQEHKC-UHFFFAOYSA-N 3,4,5-trimethyl-1,3-thiazol-3-ium Chemical compound CC=1SC=[N+](C)C=1C LTPCOIDSGQEHKC-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- UKJRKKQWBUZLPP-UHFFFAOYSA-N 3-methyl-1,3-benzothiazol-3-ium Chemical compound C1=CC=C2[N+](C)=CSC2=C1 UKJRKKQWBUZLPP-UHFFFAOYSA-N 0.000 description 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GCZVYYLOGPRVOB-UHFFFAOYSA-N 1,3-diphenylimidazolidin-1-ium;chloride Chemical compound [Cl-].C1C[NH+](C=2C=CC=CC=2)CN1C1=CC=CC=C1 GCZVYYLOGPRVOB-UHFFFAOYSA-N 0.000 description 2
- CPPGZWWUPFWALU-UHFFFAOYSA-N 1-isocyanato-3-methylbenzene Chemical compound CC1=CC=CC(N=C=O)=C1 CPPGZWWUPFWALU-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000001518 isoselenocyanato group Chemical group *N=C=[Se] 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 1
- CDKWLYGGKXMYSX-UHFFFAOYSA-M 3-methyl-1,3-benzothiazol-3-ium;chloride Chemical compound [Cl-].C1=CC=C2[N+](C)=CSC2=C1 CDKWLYGGKXMYSX-UHFFFAOYSA-M 0.000 description 1
- SGYIRNXZLWJMCR-UHFFFAOYSA-M 3-methyl-1,3-benzothiazol-3-ium;iodide Chemical compound [I-].C1=CC=C2[N+](C)=CSC2=C1 SGYIRNXZLWJMCR-UHFFFAOYSA-M 0.000 description 1
- SEBIXVUYSFOUEL-UHFFFAOYSA-N 5-methyl-1,3-benzothiazole Chemical compound CC1=CC=C2SC=NC2=C1 SEBIXVUYSFOUEL-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- BITXABIVVURDNX-UHFFFAOYSA-N isoselenocyanic acid Chemical compound N=C=[Se] BITXABIVVURDNX-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- JOWQNXIISCPKBK-UHFFFAOYSA-M magnesium;1,3,5-trimethylbenzene-6-ide;bromide Chemical compound [Mg+2].[Br-].CC1=CC(C)=[C-]C(C)=C1 JOWQNXIISCPKBK-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702037295 DE2037295A1 (de) | 1970-07-28 | 1970-07-28 | Verfahren zur Herstellung von Paraban saurederivaten |
| AT646671A AT320665B (de) | 1970-07-28 | 1971-07-26 | Verfahren zur Herstellung von Parabansäure-, Monothioparabansäure- und Dithioparabansäure-Derivaten |
| IT5189271A IT942144B (it) | 1970-07-28 | 1971-07-26 | Procedimento per la produzione di derivati di acidi parabanici e prodotti cosi ottenuti |
| CH1106471A CH563991A5 (enrdf_load_stackoverflow) | 1970-07-28 | 1971-07-27 | |
| NL7110425A NL7110425A (enrdf_load_stackoverflow) | 1970-07-28 | 1971-07-28 | |
| BE770600A BE770600A (fr) | 1970-07-28 | 1971-07-28 | Procede de preparation de derives de l'acide parabanique, de l'acide thioparabanique et de l'acide selenoparabanique |
| GB3547871A GB1354175A (en) | 1970-07-28 | 1971-07-28 | Process for the production of parabanic acid derivatives |
| FR7127700A FR2103787A5 (enrdf_load_stackoverflow) | 1970-07-28 | 1971-07-28 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702037295 DE2037295A1 (de) | 1970-07-28 | 1970-07-28 | Verfahren zur Herstellung von Paraban saurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2037295A1 true DE2037295A1 (de) | 1972-02-10 |
Family
ID=5778076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702037295 Pending DE2037295A1 (de) | 1970-07-28 | 1970-07-28 | Verfahren zur Herstellung von Paraban saurederivaten |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT320665B (enrdf_load_stackoverflow) |
| BE (1) | BE770600A (enrdf_load_stackoverflow) |
| CH (1) | CH563991A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2037295A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2103787A5 (enrdf_load_stackoverflow) |
| GB (1) | GB1354175A (enrdf_load_stackoverflow) |
| IT (1) | IT942144B (enrdf_load_stackoverflow) |
| NL (1) | NL7110425A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2743517A1 (de) * | 1977-09-28 | 1979-04-05 | Bayer Ag | Polyparabansaeurederivate |
-
1970
- 1970-07-28 DE DE19702037295 patent/DE2037295A1/de active Pending
-
1971
- 1971-07-26 AT AT646671A patent/AT320665B/de not_active IP Right Cessation
- 1971-07-26 IT IT5189271A patent/IT942144B/it active
- 1971-07-27 CH CH1106471A patent/CH563991A5/xx not_active IP Right Cessation
- 1971-07-28 GB GB3547871A patent/GB1354175A/en not_active Expired
- 1971-07-28 FR FR7127700A patent/FR2103787A5/fr not_active Expired
- 1971-07-28 BE BE770600A patent/BE770600A/xx unknown
- 1971-07-28 NL NL7110425A patent/NL7110425A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7110425A (enrdf_load_stackoverflow) | 1972-02-01 |
| AT320665B (de) | 1975-02-25 |
| IT942144B (it) | 1973-03-20 |
| BE770600A (fr) | 1971-12-01 |
| CH563991A5 (enrdf_load_stackoverflow) | 1975-07-15 |
| FR2103787A5 (enrdf_load_stackoverflow) | 1972-04-14 |
| GB1354175A (en) | 1974-06-05 |
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