Dimethylformamide → 4-(Chlorosulphonyl)benzoyl chloride

HRID 643997

Reaction equation

HRID 643997 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[Cl:7][S:8]([C:11]1[CH:19]=[CH:18]C(C(O)=O)=[CH:13][CH:12]=1)(=[O:10])=[O:9].CN(C=O)C>C(Cl)Cl>[Cl:7][S:8]([C:11]1[CH:19]=[CH:18][C:1]([C:2]([Cl:4])=[O:3])=[CH:13][CH:12]=1)(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 820244-(Chlorosulphonyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.179 g, 9.29 mmol) is added to a suspension of 4-chlorosulfonyl-benzoic acid (1.025 g, 4.64 mmol) in 10 mL of DCM at RT. A drop of DMF is added. Stirring is continued for 2.5 days. A pale yellow solution results. The reaction mixture is concentrated under vacuum. Toluene is added and the mixture is concentrated under vacuum again. This last process is repeated twice more, and the mixture is finally dried under vacuum to give 4-chlorosulfonyl-benzoyl chloride as a pale yellow solid.

Workup

  1. customA pale yellow solution results
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. additionToluene is added
  4. concentrationthe mixture is concentrated under vacuum again
  5. customthe mixture is finally dried under vacuum

Sources & evidence

ORD record
ord-119c53acd0124ce789c798d70f4fa53c
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Linked notes

Loading…