Reaction #74174

Reaction equation

N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-benzenesulfonamide

DIPEA

2-methoxyethoxymethyl chloride

→

N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzene-sulfonamide

Yield 62.3%

Solvents

DCM

DCM

Conditions

Workup

1. 1
   Washwashed with water and brine
2. 2
   Dryingdried over Na2SO4
3. 3
   Otherevaporated to dryness
4. 4
   OtherThe crude product was purified by chromatography on silica gel (n-hexane/ethyl acetate 7:3)

Procedure

N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-benzenesulfonamide (2.88 g, 8.293 mmol) was dissolved in dry DCM (75 mL) under nitrogen atmosphere. DIPEA (1.55 mL, 9.12 mmol, 1.1 eq) was then added, followed by 2-methoxyethoxymethyl chloride (0.98 mL, 9.12 mmol, 1.1 eq) and the mixture was stirred at room temperature for 1 h. It was then diluted with DCM and washed with water and brine, dried over Na2SO4 and evaporated to dryness. The crude product was purified by chromatography on silica gel (n-hexane/ethyl acetate 7:3) to give 2.25 g (62%) of N-(3-acetyl-2,4-difluoro-phenyl)-2,5-difluoro-N-(2-methoxy-ethoxymethyl)-benzene-sulfonamide as a yellow oil.

Source