Acetic Anhydride → Ethyl 2-formamidothiazol-4-acetate

HRID 261845

반응식

HRID 261845 반응식
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1>C(O)=O>[CH:1]([NH:8][C:9]1[S:10][CH:11]=[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1)=[O:3]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 178470764HCID 178470764, 화합물

생성물 1

HCID 688091Ethyl 2-formamidothiazol-4-acetate

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

To acetic anhydride (384 ml.) was added dropwise formic acid (169.2 ml.) over 15 to 20 minutes under cooling below 35° C., and the mixture was stirred for 1 hour at 55° to 60° C. To the mixture was added ethyl 2-(2-aminothiazol-4-yl)acetate, which can be represented as ethyl 2-(2-imino-2,3-dihydrothiazol-4yl)acetate, (506 g.) over 15 to 20 minutes under ice-cooling and stirring, and then the mixture was stirred for 1 hour at room temperature. After the reaction, the solvents were distilled off. To the residue was added diisopropyl ether (2500 ml.), and the mixture was stirred for 1 hour at room temperature. The precipitates were collected by filtration, washed with diisopropyl ether and then dried to give ethyl 2-(2-formylaminothiazol-4-yl)acetate, which can be represented as ethyl 2-(2-formylimino-2,3-dihydrothiazol-4-yl)acetate, (451.6 g.), mp 125° to 126° C. The remaining filtrate was concentrated, and the residue was washed with diisopropyl ether (500 ml.) and then dried to give further the same object compound (78.5 g.).

후처리

  1. temperatureunder cooling below 35° C.
  2. temperaturecooling
  3. stirringstirring
  4. stirringthe mixture was stirred for 1 hour at room temperature
  5. customAfter the reaction
  6. distillationthe solvents were distilled off
  7. additionTo the residue was added diisopropyl ether (2500 ml.)
  8. stirringthe mixture was stirred for 1 hour at room temperature
  9. filtrationThe precipitates were collected by filtration
  10. washwashed with diisopropyl ether
  11. customdried

출처 및 근거

ORD 기록
ord-4a410dee93af464c84f69c7ca85003ae
출처 데이터셋
uspto-grants-1979_05
특허 번호
US04152433

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