Methanesulfonyl chloride → HCID 19886265, compound

HRID 654796Notes

Reaction equation

HRID 654796 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]([NH2:23])=[N:9]2)=[CH:4][CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>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]([NH:23][S:25]([CH3:24])(=[O:27])=[O:26])=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 10782725HCID 10782725, compound

Product 1

HCID 19886265HCID 19886265, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]pyrazol-3-amine (0.8 g) and methanesulfonyl chloride (0.224 ml) in pyridine (8 ml) was stirred at ambient temperature for 2 hours. Pyridine was evaporated, and the residue was dissolved in ethyl acetate, washed with water and dilute hydrochloric acid, dried, and concentrated. The residual oil (1.1 g) was purified by column chromatography on silica gel (20 g) eluting with a mixture of toluene and ethyl acetate (2:1). The product (0.74 g) was recrystallized from ethanol to give pale brown crystals of N-{1-(4-fluorophenyl)-5-[4-(methylsulfonyl)phenyl]-3-pyrazolyl}methanesulfonamide (0.62 g).

Workup

  1. customPyridine was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and dilute hydrochloric acid
  4. customdried
  5. concentrationconcentrated
  6. customThe residual oil (1.1 g) was purified by column chromatography on silica gel (20 g)
  7. washeluting with a mixture of toluene and ethyl acetate (2:1)
  8. customThe product (0.74 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-9fc855777a4b4778a6ac7aad7d1c7c69
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

Loading…