N-bromobutanimide → 2-Acetoxy-5-bromo-N-(5-bromo-4-[(1,1-dimethyl)ethyl]thiazol-2-yl)benzamide

HRID 644433Notes

Reaction equation

HRID 644433 reaction equation
[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:6]=1[C:7]([NH:9][C:10]1[S:11][CH:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[N:14]=1)=[O:8])(=[O:3])[CH3:2].[Br:24]N1C(=O)CCC1=O>C(#N)C>[C:1]([O:4][C:5]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][C:6]=1[C:7]([NH:9][C:10]1[S:11][C:12]([Br:24])=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[N:14]=1)=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 85823490Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl]thiazol-2-yl}benzamide

Product 1

HCID 866026792-Acetoxy-5-bromo-N-(5-bromo-4-[(1,1-dimethyl)ethyl]thiazol-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Acetoxy-5-bromo-N-{4-[(1,1-dimethyl)ethyl]thiazol-2-yl}benzamide (compound of Example 181(2); 0.20 g, 0.50 mmol) was dissolved in acetonitrile (10 mL). N-Bromosuccinimide (97.9 mg, 0.55 mmol) was added, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound as a crude product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0fc3733fe9bb456ca51e5d34f47c9cee
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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