Bromomethyl 4-methoxyphenyl ketone → 4-(4-Methoxy-phenyl)-2-methyl-thiazole

HRID 415662

Reaction equation

HRID 415662 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=O>O>[CH3:16][O: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

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 2723949Thioacetamide

Product 1

HCID 7687654-(4-Methoxy-phenyl)-2-methyl-thiazoleYield 69.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of thioacetamide (16.0 g, 213 mmol) and 2-Bromo-1-(4-methoxy-phenyl)-ethanone (4.0 g, 17.5 mmol) was heated at 140° C. for 24 h under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (230-400 M, 1% EtOAc-Hexane) to get the desired product (2.5 g, 69%).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified over silica gel (230-400 M, 1% EtOAc-Hexane)

Sources & evidence

ORD record
ord-c282c692430b4d6ba3c8fa092613e5a3
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Linked notes

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