Chloroacetyl chloride → Sbb029873

HRID 1056845ノート

反応式

HRID 1056845 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 699491Sbb029873収率 84%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4506a47132d041c58e818cbaafbb1e69
出典データセット
uspto-grants-2016_07
特許番号
US09399647B2

反応ノート

読み込み中…