Bromomethyl 3-methoxyphenyl ketone → 4-(3-Methoxyphenyl)-2-methyl-1,3-thiazole

HRID 538621Notes

Reaction equation

HRID 538621 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].Br[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=O>O>[CH3:16][O:15][C:11]1[CH:10]=[C:9]([C:7]2[N:4]=[C:1]([CH3:2])[S:3][CH:6]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 101294Bromomethyl 3-methoxyphenyl ketoneHCID 2723949Thioacetamide

Product 1

HCID 192402834-(3-Methoxyphenyl)-2-methyl-1,3-thiazoleYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of thioacetamide (8.0 g, 106.0 mmol) and 2-bromo-1-(3-methoxy-phenyl)-ethanone (2.0 g, 8.81 mmol) was heated at 140° C. for 6 h under nitrogen atmosphere. After completion of the reaction mixture (TLC monitoring), water (50 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, 2% EtOAc-Hexane) to get the desired product (1.5 g, 83%).

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, 2% EtOAc-Hexane)

Sources & evidence

ORD record
ord-f7cdb90aa4ed494686cb82b2e3a88876
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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