Methanesulfonyl chloride → HCID 10383478, compound

HRID 1087220Notes

Reaction equation

HRID 1087220 reaction equation
FC1C=C(F)C=CC=1S[C:10]1[CH:11]=[C:12]([C:19](=[O:22])[CH2:20]C)[CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O.[CH3:23][N:24](CC(C1C=CC=CC=1)=O)[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=1[F:32].[CH3:42][S:43](Cl)(=[O:45])=[O:44]>N1C=CC=CC=1>[C:19]([C:12]1[CH:13]=[CH:14][C:15]([NH:16][S:43]([CH3:42])(=[O:45])=[O:44])=[C:10]([N:24]([CH3:23])[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])[CH:11]=1)(=[O:22])[CH3:20]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 11723692HCID 11723692, compoundHCID 86744933HCID 86744933, compound

Product 1

HCID 10383478HCID 10383478, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4'-amino-3'-[N-methyl-N-(2,4-difluorophenyl)aminoacetophenone (1.2 g) and methanesulfonyl chloride (0.6 g) in pyridine was stirred at room temperature for 7 hours. The mixture was evaporated and the residue was stirred with 5% sodium hydroxide (30 ml) overnight. The mixture was washed with toluene, and the aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was concentrated and the residue was recrystallized from ethanol to give pale brown prisms of 4'-acetyl2'-[N-methyl-N-(2,4-difluorophenyl)amino]methanesulfonanilide (0.49 g).

Workup

  1. customThe mixture was evaporated
  2. stirringthe residue was stirred with 5% sodium hydroxide (30 ml) overnight
  3. washThe mixture was washed with toluene
  4. extractionextracted with ethyl acetate
  5. concentrationThe extract was concentrated
  6. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-d77c0fc4c85941808a0b38baef61df50
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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