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

HRID 1984565노트

반응식

HRID 1984565 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) 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).

후처리

  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

출처 및 근거

ORD 기록
ord-e691464e15f142ee85c6955bc1ffd3b0
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07544700B2

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