Methanesulfonyl chloride → 4'-Cyano-2'-(2,4-difluorophenylamino)methanesulfonanilide

HRID 1087210Notes

Reaction equation

HRID 1087210 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18].[CH3:19][S:20](Cl)(=[O:22])=[O:21]>N1C=CC=CC=1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][S:20]([CH3:19])(=[O:22])=[O:21])=[C:3]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 198177244-Amino-3-(2,4-difluorophenylamino)benzonitrile

Product 1

HCID 198177204'-Cyano-2'-(2,4-difluorophenylamino)methanesulfonanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-amino-3-(2,4-difluorophenylamino)benzonitrile (1.2 g) and methanesulfonyl chloride (0.45 ml) in pyridine (12 ml) was stirred for 4 hours at room temperature. Pyridine was evaporated and the residue was stirred with an aqueous solution of sodium hydroxide (5%; 40 ml) for 10 minutes. The solution was washed with toluene, acidified to pH 3 with hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried and evaporated to dryness. The residue (1.4 g) was recrystallized from ethanol to give colorless prisms of 4'-cyano-2'-(2,4-difluorophenylamino)methanesulfonanilide (1.2 g).

Workup

  1. customPyridine was evaporated
  2. stirringthe residue was stirred with an aqueous solution of sodium hydroxide (5%; 40 ml) for 10 minutes
  3. washThe solution was washed with toluene
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated to dryness
  8. customThe residue (1.4 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-8091ceaf92ca413a87b95a9711ae56d0
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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