N-bromobutanimide → N-[5-(4-Amino-3-bromo-phenyl)-4-methyl-thiazol-2-yl]acetamide

HRID 2247319Notes

Reaction equation

HRID 2247319 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:20][C:19]([NH:21][C:22](=[O:24])[CH3:23])=[N:18][C:17]=2[CH3:25])=[CH:12][CH:11]=1>CS(C)=O.O>[NH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[S:20][C:19]([NH:21][C:22](=[O:24])[CH3:23])=[N:18][C:17]=2[CH3:25])=[CH:14][C:15]=1[Br:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 85861718N-[5-(4-amino-phenyl)-4-methyl-thiazol-2-yl]-acetamide

Product 1

HCID 85861724N-[5-(4-Amino-3-bromo-phenyl)-4-methyl-thiazol-2-yl]acetamide

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

NBS (2.52 g, 14.7 mmol) is added to a stirred solution of N-[5-(4-amino-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 1a) (3.5 g, 14.7 mmol) in dry dimethylsulphoxide (50 ml) at 10° C. After 10 minutes the solution is diluted with water (200 ml) and the resulting precipitate is removed by filtration. Crystallisation from ethyl acetate—methanol affords the title compound. MH+ (TOF, MS ES+): 325.9, 328.9

Workup

  1. customthe resulting precipitate is removed by filtration
  2. customCrystallisation from ethyl acetate—methanol

Sources & evidence

ORD record
ord-a5a01b7dc7304e6585523e665f245d6f
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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