Water → HCID 10644056, compound

HRID 1899081Notes

Reaction equation

HRID 1899081 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([C:13](Cl)=[O:14])=[CH:10][C:9]=2[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.[CH3:26][NH2:27].O1CCCC1.O>C(OCC)(=O)C>[CH3:26][NH:27][C:13]([C:11]1[S:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[C:9]([C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[CH:10]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6329MethylamineHCID 8028TetrahydrofuranHCID 23372722HCID 23372722, compound

Product 1

HCID 10644056HCID 10644056, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(4-Fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carbonyl chloride (1.4 g) was added to a stirred mixture of methylamine (25% in water, 2 ml), tetrahydrofuran (15 ml) and water (5 ml) at 5° C. The mixture was stirred at room temperature for 2 hours, diluted with ethyl acetate, washed with water, and concentrated to dryness. The residue was purified by column chromatography on silica gel (20 g) eluting with a mixture of chloroform and ethyl acetate (1:1). The purified powder (1.1 g) was crystallized from diethyl ether to give colorless crystals of N-methyl-5-(4-fluorophenyl)-4-[4-(methylsulfonyl)phenyl]thiophene-2-carboxamide (1.0 g).

Workup

  1. washwashed with water
  2. concentrationconcentrated to dryness
  3. customThe residue was purified by column chromatography on silica gel (20 g)
  4. washeluting with a mixture of chloroform and ethyl acetate (1:1)
  5. customThe purified powder (1.1 g) was crystallized from diethyl ether

Sources & evidence

ORD record
ord-f7677265158e4e59b7b3abab20eaadba
Source dataset
uspto-grants-1996_11
Patent number
US05571810

Reaction notes

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