Methanesulfonyl chloride → HCID 10472404, compound

HRID 1087205Notes

Reaction equation

HRID 1087205 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=1[F:19].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])=[C:3]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:13]=2[F:19])[CH:4]=1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10378008HCID 10378008, compound

Product 1

HCID 10472404HCID 10472404, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4'-amino-3'-(2,4-difluorophenylamino)acetophenone (1.7 g) and methanesulfonyl chloride (0.9 g) in pyridine (17 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%) for 30 minutes. The solution was washed with toluene, acidified to pH 3 with hydrochloric acid, and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium bicarbonate, dried, and concentrated under reduced pressure. The syrupy residue (1.8 g) was crystallized from ethanol to give pale yellow crystals of 4'-acetyl-2'-(2,4-difluorophenylamino)methanesulfonanilide (1.3 g).

Workup

  1. customPyridine was evaporated
  2. stirringthe residue was stirred with an aqueous solution of sodium hydroxide (5%) for 30 minutes
  3. washThe solution was washed with toluene
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium bicarbonate
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe syrupy residue (1.8 g) was crystallized from ethanol

Sources & evidence

ORD record
ord-d9434fbdde084013836e46ee42d0a47a
Source dataset
uspto-grants-1991_07
Patent number
US05034417

Reaction notes

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