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

HRID 2245300Notes

Reaction equation

HRID 2245300 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) was added dropwise to a solution of the above compound (1a) (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 (1b); 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).

Workup

  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

Sources & evidence

ORD record
ord-8be4b061a9334ccfa1e7077ebaba41a3
Source dataset
uspto-grants-2010_03
Patent number
US07683078B2

Reaction notes

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