Water → N-[2-(Chloroacetyl)-5-fluorophenyl]-N-methylformamide

HRID 358664Notes

Reaction equation

HRID 358664 reaction equation
S(Cl)([Cl:4])(=O)=O.[C:6]([C:9]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:10]=1[N:11]([CH3:14])[CH:12]=[O:13])(=[O:8])[CH3:7].O>ClCCl>[Cl:4][CH2:7][C:6]([C:9]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:10]=1[N:11]([CH3:14])[CH:12]=[O:13])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 231281532'-acetyl-5'-fluoro-N-methylformanilide

Product 1

HCID 23128132N-[2-(Chloroacetyl)-5-fluorophenyl]-N-methylformamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of sulphuryl chloride (20.6 ml) in dichloromethane (30 ml) was added dropwise over a period of 45 minutes to the solution of 2'-acetyl-5'-fluoro-N-methylformanilide whilst maintaining the temperature below 2° with ice/water cooling under a nitrogen atmosphere. The mixture was stirred for 3 hours maintaining the temperature below 2°. Water (80 ml) was added dropwise over 15 minutes maintaining the temperature below 10°. The dichloromethane layer was separated and dried over magnesium sulphate to give a solution of 2'-(2-chloroacetyl)-5'-fluoro-N-methylformanilide.

Workup

  1. temperaturemaintaining the temperature below 2°
  2. temperaturemaintaining the temperature below 10°
  3. customThe dichloromethane layer was separated
  4. dry with materialdried over magnesium sulphate

Sources & evidence

ORD record
ord-4dcfe2d08b144f06908700d2cfb0a940
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…