Sodium Bicarbonate → 2-Ethyl-4-(4-nitrobenzyl)-1,3-thiazole

HRID 30665Notes

Reaction equation

HRID 30665 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[C:15](=[S:19])([NH2:18])[CH2:16][CH3:17].C(=O)([O-])O.[Na+]>C(O)C>[CH2:16]([C:15]1[S:19][CH:2]=[C:3]([CH2:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=2)[N:18]=1)[CH3:17]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2760628PropanethioamideHCID 122323022-Propanone, 1-bromo-3-(4-nitrophenyl)-

Product 1

HCID 692091612-Ethyl-4-(4-nitrobenzyl)-1,3-thiazoleYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-bromo-3-(4-nitrophenyl)-2-propanone (0.50 g), propanethioamide (0.17 g) and ethanol (10 mL) was heated under reflux for 2 hrs. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and 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 to give 2-ethyl-4-(4-nitrobenzyl)-1,3-thiazole as a colorless oil (0.45 g, yield 96%) from a fraction eluted with hexane-ethyl acetate (9:1-4:1, v/v).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ef58f0ac0db24699b66641ec805c466d
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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