Acetic Anhydride → 2-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester

HRID 2353829

반응식

HRID 2353829 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:16]([NH:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:18])[CH3:17]

참가 물질

3

반응물 2

HCID 7918Acetic AnhydrideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

생성물 1

HCID 986822-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester수율 81%

실험 절차

Ethyl 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (100 g, 444 mmol) and acetic anhydride (227 g, 2.2 mol) were heated at reflux for ˜15 minutes and then allowed to cool to room temperature overnight. The reaction mixture containing white solid was filtered. The solid was rinsed with water (2 L) and dried in a vacuum oven for several hours at ˜45° C. to yield a white crystalline solid (96 g, 81%). 1H NMR (DMSO-d6) δ 4.26 (q, 2H), 2.69 (t, 2H), 2.57 (t, 2H), 2.20 (s, 3H), 1.70 (m, 4H), 1.30 (t, 3H), LCMS RT=3.48 min, [M+H]+=268.0.

후처리

  1. temperatureat reflux for ˜15 minutes
  2. additionThe reaction mixture containing white solid
  3. filtrationwas filtered
  4. washThe solid was rinsed with water (2 L)
  5. customdried in a vacuum oven for several hours at ˜45° C.

출처 및 근거

ORD 기록
ord-99bade2e5eb84782bfaf25398788e8e9
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750017B2

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