Chloroacetyl chloride → Sbb029873

HRID 1056845노트

반응식

HRID 1056845 반응식
[NH2:1][C:2]1[S:3][C:4]2[CH2:13][CH2:12][CH2:11][CH2:10][C:5]=2[C:6]=1[C:7]([NH2:9])=[O:8].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)Cl>[Cl:21][CH2:22][C:23]([NH:1][C:2]1[S:3][C:4]2[CH2:13][CH2:12][CH2:11][CH2:10][C:5]=2[C:6]=1[C:7]([NH2:9])=[O:8])=[O:24]

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2902232-Amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide

생성물 1

HCID 699491Sbb029873수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of 2-amino-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide (30 g, 0.153 mol) and triethylamine (18.5 g, 0.183 mol) in DCM (200 ml) was added chloro-acetyl chloride (20.57 g, 0.183 mol) slowly at 0° C., and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was concentrated to half of the volume to afford the solid product which was filtered, washed with 10 ml of DCM and dried to provide 2-(2-chloro-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid amide (35 g, 84%) as off-white solid. 1H NMR (400 MHz, DMSO-d6): δ 1.65-1.75 (m, 4H), 2.58-2.72 (m, 4H), 4.49 (s, 2H), 7.29 (s, 1H), 7.42 (s, 1H), 12.23 (s, 1H); LC-MS: [M+H]=272.8, 275.1, 257.9 & 255.9 m/z.

후처리

  1. concentrationThe reaction mixture was concentrated to half of the volume
  2. customto afford the solid product which
  3. filtrationwas filtered
  4. washwashed with 10 ml of DCM
  5. customdried

출처 및 근거

ORD 기록
ord-4506a47132d041c58e818cbaafbb1e69
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399647B2

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