Chlorosulfonic acid → 5-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride

HRID 1869265ノート

反応式

HRID 1869265 の反応式
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([C:11]([NH:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][C:15]2[S:16][C:17]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:18][CH:19]=2)=[O:12])=[CH:20][CH:21]=1

参加物

4

反応物 2

HCID 24638Chlorosulfonic acidHCID 7222864-chloro-N-(thiophen-2-ylmethyl)benzamide

生成物 1

HCID 27357135-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride収率 63%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Chlorosulfonic acid (20.1 ml, 198 mmol) in CH2Cl2 (80 ml) is added dropwise to a solution of 1a (10 g, 40 mmol) in CH2Cl2 (500 ml) at −80° C. The mixture is allowed to reach room temperature in 5 h. The reaction mixture is poured on ice and quickly extracted with CH2Cl2. The organic layer is dried over MgSO4 and the solvent is evaporated to dryness which affords 8.8 g (63%) of desired sulfonyl chloride 1b; mp 133-35° C., 1H NMR (DMSO) δ 9.21 (t, J=6.4 Hz, 1H), 7.87 (d, J=8.67 Hz, 2H), 7.53 (d, J=8.67 Hz, 2H), 6.91 (d, J=3.9 Hz, 1H), 6.77 (d, J=3.39 Hz, 1H), 4.53 (d, J=3.77 Hz, 2H).

後処理

  1. additionThe reaction mixture is poured on ice
  2. extractionquickly extracted with CH2Cl2
  3. dry with materialThe organic layer is dried over MgSO4
  4. customthe solvent is evaporated to dryness which

出典と根拠

ORDレコード
ord-38aae4b85edc4e0ca4557297d3862d86
出典データセット
uspto-grants-2009_12
特許番号
US07638538B1

反応ノート

読み込み中…