Bromoacetone → 4-Methyl-2-(4-nitrobenzyl)-1,3-thiazole

HRID 30638

Reaction equation

HRID 30638 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11](=[S:13])[NH2:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:15][C:16](=O)[CH3:17]>C(O)C>[CH3:17][C:16]1[N:12]=[C:11]([CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[S:13][CH:15]=1

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 27773372-(4-Nitrophenyl)thioacetamide

Product 1

HCID 692091384-Methyl-2-(4-nitrobenzyl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-nitrophenyl)ethanethioamide (0.50 g), 1-bromo-2-propanone (0.43 g) and ethanol (20 mL) was heated under reflux for 1 hr. The reaction mixture was concentrated, and saturated aqueous sodium hydrogen carbonate was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 4-methyl-2-(4-nitrobenzyl)-1,3-thiazole was obtained as pale-yellow crystals (0.37 g, yield 63%) from a fraction eluted with hexane-ethyl acetate (2:1-1:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave colorless prism crystals. melting point: 81-82° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionsaturated aqueous sodium hydrogen carbonate was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6e90ae0f47444898ac20281d8b2f1b85
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

Loading…