Dimethylformamide → 3-(Methanesulfonyl)benzoyl chloride

HRID 716735Notes

Reaction equation

HRID 716735 reaction equation
CN(C=O)C.[C:6](Cl)(=O)[C:7]([Cl:9])=[O:8].[CH3:12][S:13]([C:16]1[CH:17]=C([CH:22]=[CH:23][CH:24]=1)C(O)=O)(=[O:15])=[O:14]>C(Cl)(Cl)Cl>[CH3:12][S:13]([C:16]1[CH:17]=[C:6]([CH:22]=[CH:23][CH:24]=1)[C:7]([Cl:9])=[O:8])(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2203803-Methanesulfonylbenzoic acid

Product 1

HCID 221378393-(Methanesulfonyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

DMF (0.4 mL) and oxalyl chloride (1.90 g) were added to a solution of 3-(methylsulfonyl)benzoic acid (2.00 g) in CHCl3 (including amylene, 40 mL) in a nitrogen gas flow under ice cooling, followed by stirring at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure to yield a crude product as a yellow solid, which was used in the subsequent reaction.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3d2d800ab378408cb99ebe1820faf0a2
Source dataset
uspto-grants-2015_11
Patent number
US09193695B2

Reaction notes

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