1-Bromo-2-butanone → 4-Ethyl-2-(4-nitrobenzyl)-1,3-thiazole

HRID 30636

Reaction equation

HRID 30636 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)[CH2:17][CH3:18]>C(O)C>[CH2:17]([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)[CH3:18]

Participants

4

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 27773372-(4-Nitrophenyl)thioacetamide

Product 1

HCID 692078474-Ethyl-2-(4-nitrobenzyl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-nitrophenyl)ethanethioamide (1.50 g), 1-bromo-2-butanone (1.27 g) and ethanol (50 mL) was heated under reflux for 30 min. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and 4-ethyl-2-(4-nitrobenzyl)-1,3-thiazole was obtained as a brown oil (1.59 g, yield 84%) from a fraction eluted with hexane-ethyl acetate (7:1-4:1, v/v).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added to the residue
  5. washThe mixture was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e0f339386dd34ad9b348c21780d8528a
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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