Reaction #79280

Reaction equation

HCl

2,4-difluoro-N-(2-hydroxyethyl)benzamide

triethylamine

methanesulfonyl chloride

→

2-[(2,4-difluorobenzoyl)amino]ethyl methanesulfonate

Yield 72.1%

Solvents

CH2Cl2

ethyl acetate

Conditions

Workup

1. 1
   Otherto quench
2. 2
   Otherthe reaction
3. 3
   Washwashed with saturated NaHCO3 (100 mL) and saturated NaCl (100 mL)
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   OtherPurification by column chromatography (hexanes:EtOAc 4:1)

Procedure

To a solution of 2,4-difluoro-N-(2-hydroxyethyl)benzamide (299 mg, 1.49 mmol) and triethylamine (302 mg, 2.98 mmol) in CH2Cl2 under nitrogen at 0° C. was added methanesulfonyl chloride (335 mg, 2.98 mmol) The reaction mixture was stirred for 1 h at 0° C. 1 N HCl (5 mL) was added to quench the reaction and the solution was diluted with ethyl acetate (100 mL), washed with saturated NaHCO3 (100 mL) and saturated NaCl (100 mL), dried over MgSO4, filtered and concentrated in vacuo. Purification by column chromatography (hexanes:EtOAc 4:1) yielded 2-[(2,4-difluorobenzoyl)amino]ethyl methanesulfonate (300 mg, 72%) as a clear liquid.

Source