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

HRID 1869265노트

반응식

HRID 1869265 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-38aae4b85edc4e0ca4557297d3862d86
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638538B1

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