Methanesulfonyl chloride → HCID 19886126, compound

HRID 654792Notes

Reaction equation

HRID 654792 reaction equation
[OH: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.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:8]([C:5]3[CH:6]=[CH:7][C:2]([O:1][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:3][CH:4]=3)[N:9]=[C:10]([C:23]#[N:25])[CH:11]=2)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 19886134HCID 19886134, compound

Product 1

HCID 19886126HCID 19886126, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1-(4-hydroxyphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carboxamide (1.3 g) and methanesulfonyl chloride (2.5 g) in pyridine (20 ml) was stirred at 50° C. for 5 hours. The solvent was evaporated, and dilute hydrochloric acid and ethyl acetate was added to the residue. The organic layer was washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel (20 g) eluting with a mixture of chloroform and methanol (20:1) to give crystals of 5-[4-(methylsulfonyl)phenyl]-1-[4-(methylsulfonyloxy)-phenyl]pyrazole-3-carbonitrile (0.79 g).

Workup

  1. customThe solvent was evaporated
  2. additiondilute hydrochloric acid and ethyl acetate was added to the residue
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (20 g)
  7. washeluting with a mixture of chloroform and methanol (20:1)

Sources & evidence

ORD record
ord-ec0d7e1f821846e2b965150b3d3e2e76
Source dataset
uspto-grants-1992_07
Patent number
US05134142

Reaction notes

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