Imidazole → Acetamide, N-[5-[3-(1H-imidazol-1-YL)-4-(methylsulfonyl)phenyl]-4-methyl-2-thiazolyl]-

HRID 601612Notes

Reaction equation

HRID 601612 reaction equation
F[C:2]1[CH:3]=[C:4]([C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=2[CH3:21])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[N:22]1([C:2]2[CH:3]=[C:4]([C:12]3[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][C:13]=3[CH3:21])[CH:5]=[CH:6][C:7]=2[S:8]([CH3:11])(=[O:10])=[O:9])[CH:26]=[CH:25][N:24]=[CH:23]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 57351276N-[5-(3-fluoro-4-methylsulfonylphenyl)-4-methyl-1,3-thiazol-2-yl]acetamide

Product 1

HCID 53429448Acetamide, N-[5-[3-(1H-imidazol-1-YL)-4-(methylsulfonyl)phenyl]-4-methyl-2-thiazolyl]-

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

A stirred mixture of N-[5-(3-fluoro-4-methanesulfonyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide (AF1) (5.0 g, 15 mmol), imidazole (2.07 g, 30 mmol) and caesium carbonate (9.93 g, 30 mmol) in dry NMP (30 ml) is heated under argon at 135° C. for 18 hours. The reaction mixture is then poured onto water (50 ml) whereupon the titled product precipitates and is recrystalfised from ethanol-water.

Sources & evidence

ORD record
ord-8c23d3e64e344485931a955fca1f4b4f
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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