GB1234833A - 3-aminoacylamino-thiophens and process for preparing them - Google Patents
3-aminoacylamino-thiophens and process for preparing themInfo
- Publication number
- GB1234833A GB1234833A GB3243868A GB3243868A GB1234833A GB 1234833 A GB1234833 A GB 1234833A GB 3243868 A GB3243868 A GB 3243868A GB 3243868 A GB3243868 A GB 3243868A GB 1234833 A GB1234833 A GB 1234833A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methylthiophene
- carbomethoxy
- reacting
- chloroacetylamino
- amino
- 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
- 238000004519 manufacturing process Methods 0.000 title 1
- HFOFPDGUBCVRIQ-UHFFFAOYSA-N 4-methylthiophen-3-amine Chemical compound CC1=CSC=C1N HFOFPDGUBCVRIQ-UHFFFAOYSA-N 0.000 abstract 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- -1 methylimino group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical compound NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 abstract 2
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 abstract 1
- BNRUONNHGBBDEG-UHFFFAOYSA-N (E)-N-(4-methylthiophen-3-yl)but-2-enamide Chemical compound C(C=CC)(=O)NC1=CSC=C1C BNRUONNHGBBDEG-UHFFFAOYSA-N 0.000 abstract 1
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 abstract 1
- NKYZMZNNAWWQCF-UHFFFAOYSA-N 2,4-dimethylthiophen-3-amine Chemical compound CC1=CSC(C)=C1N NKYZMZNNAWWQCF-UHFFFAOYSA-N 0.000 abstract 1
- WURYWHAKEJHAOV-UHFFFAOYSA-N 2,5-dihydrothiophene Chemical compound C1SCC=C1 WURYWHAKEJHAOV-UHFFFAOYSA-N 0.000 abstract 1
- RTZFKQORWVHODG-UHFFFAOYSA-N 2-[butyl(phenylmethoxycarbonyl)amino]acetic acid Chemical compound CCCCN(CC(O)=O)C(=O)OCC1=CC=CC=C1 RTZFKQORWVHODG-UHFFFAOYSA-N 0.000 abstract 1
- FIMCOWPZXBVBIB-UHFFFAOYSA-N 2-chloro-N-(4-methylthiophen-3-yl)acetamide Chemical compound ClCC(=O)NC1=CSC=C1C FIMCOWPZXBVBIB-UHFFFAOYSA-N 0.000 abstract 1
- XSFLTBALOWBTLJ-UHFFFAOYSA-N 2-chloro-N-(4-methylthiophen-3-yl)propanamide Chemical compound CC(Cl)C(=O)NC1=CSC=C1C XSFLTBALOWBTLJ-UHFFFAOYSA-N 0.000 abstract 1
- XBLYPENZTYSJMR-UHFFFAOYSA-N 2-chloro-n-(2,4-dimethylthiophen-3-yl)acetamide Chemical compound CC1=CSC(C)=C1NC(=O)CCl XBLYPENZTYSJMR-UHFFFAOYSA-N 0.000 abstract 1
- YWUMLYIEKOMXCF-UHFFFAOYSA-N 2-chloro-n-thiophen-3-ylacetamide Chemical compound ClCC(=O)NC=1C=CSC=1 YWUMLYIEKOMXCF-UHFFFAOYSA-N 0.000 abstract 1
- KXCUFSHZVJKKQN-UHFFFAOYSA-N 3-[[2-(butylamino)acetyl]amino]-4-methylthiophene-2-carboxylic acid Chemical compound C(CCC)NCC(=O)NC1=C(SC=C1C)C(=O)O KXCUFSHZVJKKQN-UHFFFAOYSA-N 0.000 abstract 1
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical compound NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 abstract 1
- CSJWMDPBYLZFPZ-UHFFFAOYSA-N 3-isocyanothiophene Chemical compound [C-]#[N+]C=1C=CSC=1 CSJWMDPBYLZFPZ-UHFFFAOYSA-N 0.000 abstract 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005695 Ammonium acetate Substances 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229940043376 ammonium acetate Drugs 0.000 abstract 1
- 235000019257 ammonium acetate Nutrition 0.000 abstract 1
- HGPSTKPBMMGYNC-UHFFFAOYSA-N benzyl N-[2-(butylamino)acetyl]-N-(4-methylthiophen-2-yl)carbamate Chemical compound C(C1=CC=CC=C1)OC(=O)N(C(CNCCCC)=O)C=1SC=C(C1)C HGPSTKPBMMGYNC-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- RTHZEWLREYQGED-UHFFFAOYSA-N ethyl 3-[(2-chloroacetyl)amino]-4-methylthiophene-2-carboxylate Chemical compound ClCC(=O)NC1=C(SC=C1C)C(=O)OCC RTHZEWLREYQGED-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- SPKRZDZVDTWKDM-UHFFFAOYSA-N methyl 3-(2-chloropropanoylamino)-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1NC(=O)C(C)Cl SPKRZDZVDTWKDM-UHFFFAOYSA-N 0.000 abstract 1
- YUVKYHLYLVTJEN-UHFFFAOYSA-N methyl 3-[(2-chloroacetyl)amino]-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1NC(=O)CCl YUVKYHLYLVTJEN-UHFFFAOYSA-N 0.000 abstract 1
- YICRPERKKBDRSP-UHFFFAOYSA-N methyl 3-amino-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1N YICRPERKKBDRSP-UHFFFAOYSA-N 0.000 abstract 1
- PWSUQEJRFKOGJV-UHFFFAOYSA-N methyl 3-formamido-4-methylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC=C(C)C=1NC=O PWSUQEJRFKOGJV-UHFFFAOYSA-N 0.000 abstract 1
- FFBGJTDOWCDBAY-UHFFFAOYSA-N methyl 3-isocyano-4-methylthiophene-2-carboxylate Chemical compound [N+](#[C-])C1=C(SC=C1C)C(=O)OC FFBGJTDOWCDBAY-UHFFFAOYSA-N 0.000 abstract 1
- XLFOHJYHWRZPSJ-UHFFFAOYSA-N methyl 4-[(2-chloroacetyl)amino]-3,5-dimethylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C)=C(NC(=O)CCl)C=1C XLFOHJYHWRZPSJ-UHFFFAOYSA-N 0.000 abstract 1
- HVBIUVQBADYWDO-UHFFFAOYSA-N methyl 4-[(2-chloroacetyl)amino]-3-methyl-2,3-dihydrothiophene-5-carboxylate Chemical compound ClCC(=O)NC1=C(SCC1C)C(=O)OC HVBIUVQBADYWDO-UHFFFAOYSA-N 0.000 abstract 1
- XGRGVSLMGRDGLN-UHFFFAOYSA-N methyl 4-[(2-chloroacetyl)amino]-5-methylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(C)=C1NC(=O)CCl XGRGVSLMGRDGLN-UHFFFAOYSA-N 0.000 abstract 1
- LIBZOVHLJDICEY-UHFFFAOYSA-N methyl 4-[2-[butyl(phenylmethoxycarbonyl)amino]acetyl]-3,5-dimethylthiophene-2-carboxylate Chemical compound C(C1=CC=CC=C1)OC(=O)N(CCCC)CC(=O)C1=C(SC(=C1C)C(=O)OC)C LIBZOVHLJDICEY-UHFFFAOYSA-N 0.000 abstract 1
- KUUQEVITZAPQJB-UHFFFAOYSA-N methyl 4-[[2-(diethylamino)acetyl]amino]-3-methyl-2,3-dihydrothiophene-5-carboxylate Chemical compound CCN(CC)CC(=O)NC1=C(C(=O)OC)SCC1C KUUQEVITZAPQJB-UHFFFAOYSA-N 0.000 abstract 1
- GWIZXJHXFRMSQV-UHFFFAOYSA-N methyl 4-amino-3,5-dimethylthiophene-2-carboxylate Chemical compound COC(=O)C=1SC(C)=C(N)C=1C GWIZXJHXFRMSQV-UHFFFAOYSA-N 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1967F0052885 DE1643325B2 (de) | 1967-07-07 | 1967-07-07 | 3-aminoacylaminothiophene und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1234833A true GB1234833A (en) | 1971-06-09 |
Family
ID=7105818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3243868A Expired GB1234833A (en) | 1967-07-07 | 1968-07-08 | 3-aminoacylamino-thiophens and process for preparing them |
Country Status (14)
| Country | Link |
|---|---|
| AT (7) | AT282614B (enExample) |
| BE (1) | BE717788A (enExample) |
| CH (1) | CH504451A (enExample) |
| CS (7) | CS150587B2 (enExample) |
| DE (1) | DE1643325B2 (enExample) |
| DK (1) | DK120029B (enExample) |
| ES (1) | ES355858A1 (enExample) |
| FI (1) | FI50879C (enExample) |
| FR (2) | FR1584764A (enExample) |
| GB (1) | GB1234833A (enExample) |
| NL (1) | NL156405B (enExample) |
| NO (1) | NO122432B (enExample) |
| SE (1) | SE352639B (enExample) |
| YU (7) | YU33871B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117586223A (zh) * | 2022-08-16 | 2024-02-23 | 四川大学 | 一种酚噻嗪类化合物及其用途 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5166346A (en) * | 1987-12-11 | 1992-11-24 | Hoechst Aktiengesellschaft | Process for the preparation of thiophene derivatives and also new dihydrothiophene 1-oxides |
| CA62573S (en) | 1989-02-20 | 1989-02-28 | Raymond Rodenburgh | Double unit for retaining wall |
| DE4244069A1 (de) * | 1992-12-24 | 1994-06-30 | Hoechst Ag | Cephalosporinsalze und Verfahren zu deren Herstellung |
-
1967
- 1967-07-07 DE DE1967F0052885 patent/DE1643325B2/de active Granted
-
1968
- 1968-07-02 YU YU155668A patent/YU33871B/xx unknown
- 1968-07-04 CH CH1001468A patent/CH504451A/de not_active IP Right Cessation
- 1968-07-05 AT AT615969A patent/AT282614B/de not_active IP Right Cessation
- 1968-07-05 DK DK330768A patent/DK120029B/da not_active IP Right Cessation
- 1968-07-05 AT AT616069A patent/AT284833B/de not_active IP Right Cessation
- 1968-07-05 AT AT615669A patent/AT281810B/de not_active IP Right Cessation
- 1968-07-05 NL NL6809539A patent/NL156405B/xx not_active IP Right Cessation
- 1968-07-05 CS CS527868A patent/CS150587B2/cs unknown
- 1968-07-05 CS CS527668A patent/CS150585B2/cs unknown
- 1968-07-05 CS CS527568A patent/CS150584B2/cs unknown
- 1968-07-05 AT AT06161/69A patent/AT282615B/de not_active IP Right Cessation
- 1968-07-05 AT AT648968A patent/AT281809B/de not_active IP Right Cessation
- 1968-07-05 CS CS527768A patent/CS150586B2/cs unknown
- 1968-07-05 CS CS498368A patent/CS150583B2/cs unknown
- 1968-07-05 AT AT615869A patent/AT282613B/de not_active IP Right Cessation
- 1968-07-05 AT AT615769A patent/AT282612B/de not_active IP Right Cessation
- 1968-07-05 CS CS528071A patent/CS150589B2/cs unknown
- 1968-07-05 FI FI194668A patent/FI50879C/fi active
- 1968-07-05 CS CS527968A patent/CS150588B2/cs unknown
- 1968-07-06 ES ES355858A patent/ES355858A1/es not_active Expired
- 1968-07-08 SE SE937268A patent/SE352639B/xx unknown
- 1968-07-08 GB GB3243868A patent/GB1234833A/en not_active Expired
- 1968-07-08 NO NO271568A patent/NO122432B/no unknown
- 1968-07-08 BE BE717788D patent/BE717788A/xx not_active IP Right Cessation
- 1968-07-08 FR FR1584764D patent/FR1584764A/fr not_active Expired
- 1968-10-04 FR FR168764A patent/FR8214M/fr not_active Expired
-
1973
- 1973-09-27 YU YU256273A patent/YU33963B/xx unknown
- 1973-09-27 YU YU256373A patent/YU34043B/xx unknown
- 1973-09-27 YU YU256573A patent/YU33965B/xx unknown
- 1973-09-27 YU YU256473A patent/YU33964B/xx unknown
- 1973-09-27 YU YU256173A patent/YU33962B/xx unknown
- 1973-09-27 YU YU256073A patent/YU33961B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117586223A (zh) * | 2022-08-16 | 2024-02-23 | 四川大学 | 一种酚噻嗪类化合物及其用途 |
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