Pyridine → 2-(3-Chloromethyl-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester

HRID 1094975

반응식

HRID 1094975 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]=1[NH2:15])=[O:5])[CH3:2].N1C=CC=CC=1.CO[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1OC)[C:27](Cl)=[O:28].[CH2:35]([Cl:37])Cl>>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]=1[NH:15][C:27](=[O:28])[C:26]1[CH:30]=[CH:31][CH:32]=[C:24]([CH2:35][Cl:37])[CH:25]=1)=[O:5])[CH3:2]

참가 물질

5

반응물 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 77070Veratroyl chloride2회HCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate2회

생성물 1

HCID 666392012-(3-Chloromethyl-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester

반응 조건

온도
0 °C

실험 절차

2-Amino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester (Compound A) (4.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (2.8 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (3.0 ml) were added at 0° C., and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added, and the mixture was subjected to separatory extraction with chloroform, and the organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester as a useful intermediate (7.42 g, yield 100%).

후처리

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionthe mixture was subjected to separatory extraction with chloroform
  5. washthe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated

출처 및 근거

ORD 기록
ord-d039a63894f94c38830b00a29956f7a9
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08134015B2

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