Triethylamine → N-(2-methylsulfonyloxyethyl)-4-chlorobenzamide

HRID 2255114Notes

Reaction equation

HRID 2255114 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2339794-Chloro-N-(2-hydroxyethyl)benzamide

Product 1

HCID 19741760N-(2-methylsulfonyloxyethyl)-4-chlorobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.6 ml of methanesulfonyl chloride in 3 ml of methylene chloride is added dropwise at 0° to a solution of 1.5 g (0.0075 mol) of N-(2-hydroxyethyl)-4-chlorobenzamide and 1 ml of triethylamine in 15 ml of methylene chloride. After 15 minutes, the mixture is poured on to ice/water and extracted. There are obtained 2.1 g of N-(2-methylsulfonyloxyethyl)-4-chlorobenzamide in crystalline form which is used in the next step without further purification.

Workup

  1. extractionextracted

Sources & evidence

ORD record
ord-9e37de03ee1040238e43ac4e5fe61f57
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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