Water → 2-Bromo-5-methyl-4-phenylthiazole

HRID 2263168Notes

Reaction equation

HRID 2263168 reaction equation
[CH3:1][CH:2]([S:11][C:12]#[N:13])[C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.[BrH:15].C(O)(=O)C>>[Br:15][C:12]1[S:11][C:2]([CH3:1])=[C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[N:13]=1

Participants

4

Reactant 3

HCID 962WaterHCID 109433031-Methyl-2-oxo-2-phenylethyl thiocyanateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 496519402-Bromo-5-methyl-4-phenylthiazoleYield 73.1%

Procedure

A solution of 1-methyl-2-oxo-2-phenylethyl thiocyanate (1.00 g, 5.23 mmol) in 25% hydrogen bromide/acetic acid (10 ml) was stirred at 130° C. for 2 hours and at room temperature for 1 hour. Water was poured into the reaction solution, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give 971 mg (73.1%) of the desired product as an oil.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-9e3c9dc5035b43ec9fdeb769be70078d
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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