Methanesulfonyl chloride → HCID 10042938, compound

HRID 654782Notes

Reaction equation

HRID 654782 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:23]([NH2:25])=O)=[N:9]2)=[CH:4][CH:3]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)=[CH:11][C:10]([C:23]#[N:25])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10546370HCID 10546370, compound

Product 1

HCID 10042938HCID 10042938, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carboxamide (2.7 g) and methanesulfonyl chloride (3.4 ml) in pyridine (25 ml) was stirred at 50° C. for 6 hours. The solvent was evaporated, and ethyl acetate and water were added to the residue. The precipitates were filtered and washed with water and ethyl acetate. The filtrate was separated, and the organic layer was washed with dilute hydrochloric acid, dried and concentrated to dryness. The residue and the former precipitates were combined and recrystallized from a mixture of ethanol and ethyl acetate to give colorless crystals of 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carbonitrile (2.4 g).

Workup

  1. customThe solvent was evaporated
  2. additionethyl acetate and water were added to the residue
  3. filtrationThe precipitates were filtered
  4. washwashed with water and ethyl acetate
  5. customThe filtrate was separated
  6. washthe organic layer was washed with dilute hydrochloric acid
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe residue and the former precipitates
  10. customrecrystallized from a mixture of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-c522c6e53dca4fb0b26740b64d8bd217
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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