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

HRID 1869265Notes

Reaction equation

HRID 1869265 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-38aae4b85edc4e0ca4557297d3862d86
Source dataset
uspto-grants-2009_12
Patent number
US07638538B1

Reaction notes

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