Ammonia → 4-(4-Fluorophenyl)-2-methylthiazole

HRID 875017Notes

Reaction equation

HRID 875017 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=O.N>C(O)C>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7]2[N:4]=[C:1]([CH3:2])[S:3][CH:6]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-oneHCID 2723949Thioacetamide

Product 1

HCID 7318944-(4-Fluorophenyl)-2-methylthiazoleYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Thioacetamide (1.73 g, 23.03 mmol) was added to a solution of 2-bromo-1-(4-fluorophenyl)ethanone (5.0 g, 23.03 mmol) in ethanol (50 mL) and the reaction was refluxed at 70° C. for 4 h. The reaction mixture was then cooled to room temperature, neutralized to pH 7 with aqueous ammonia solution (20 ml), and extracted with ethyl acetate (200 mL). The combined extracts were washed with water (100 mL), dried over Na2SO4, and concentrated to provide 4-(4-fluorophenyl)-2-methylthiazole (4.0 g, 90%). 1H NMR (400 MHz, DMSO) δ 7.95-8.00 (m, 2H), 7.91 (s, 1H), 7.23-7.29 (m, 2H), 2.71 (s, 3H). MS (ESI) m/z: Calculated for C10H8FNS: 193.04. found: 194.0 (M+H)+

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. extractionextracted with ethyl acetate (200 mL)
  3. washThe combined extracts were washed with water (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8b3707a9691147f7957423ee55727c56
Source dataset
uspto-grants-2015_03
Patent number
US08981084B2

Reaction notes

Loading…