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

HRID 1984565ノート

反応式

HRID 1984565 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) was added dropwise to a solution of (63a) (10 g, 40 mmol) in CH2Cl2 (500 ml) at −80° C. The mixture was allowed to reach room temperature in 5 h. The reaction mixture was poured on ice and quickly extracted with CH2Cl2. The organic layer was dried over MgSO4 and the solvent was evaporated to dryness which afforded 8.8 g (63%) of desired sulfonyl chloride (63b); mp 133-35° C., 1H NMR (DMSO-d6) 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=3.39 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 was poured on ice
  2. extractionquickly extracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe solvent was evaporated to dryness which

出典と根拠

ORDレコード
ord-e691464e15f142ee85c6955bc1ffd3b0
出典データセット
uspto-grants-2009_06
特許番号
US07544700B2

反応ノート

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