Methanesulfonyl chloride → HCID 11796642, compound

HRID 1899090Notes

Reaction equation

HRID 1899090 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([NH2:13])=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=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]([C:8]2[S:12][C:11]([NH:13][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 104978555-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine

Product 1

HCID 11796642HCID 11796642, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thiophenamine (1.0 g) and methanesulfonyl chloride (0.27 ml) in pyridine (10 ml) was stirred overnight. Pyridine was evaporated, and the residue was dissolved in ethyl acetate, washed with water, dried and concentrated. The residue was dissolved in tetrahydrofuran (10 ml) and treated with 4N sodium hydroxide (1.8 ml) for 2 hours. Ethyl acetate and water were added and the mixture was separated. The aqueous layer was acidified and extracted with ethyl acetate. The extract was dried and concentrated to dryness. The residue (1.1 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (3:1) to give a pale brown powder of N-{5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]-2-thienyl}methanesulfonamide (0.79 g).

Workup

  1. customPyridine was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in tetrahydrofuran (10 ml)
  7. additiontreated with 4N sodium hydroxide (1.8 ml) for 2 hours
  8. additionEthyl acetate and water were added
  9. customthe mixture was separated
  10. extractionextracted with ethyl acetate
  11. customThe extract was dried
  12. concentrationconcentrated to dryness
  13. customThe residue (1.1 g) was purified by column chromatography on silica gel eluting with a mixture of toluene and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-dfa38a0127c04f068c37979c411802f5
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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