Chloroacetaldehyde → 2-(4-Nitrobenzyl)-1,3-thiazole

HRID 30639

Reaction equation

HRID 30639 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].Cl[CH2:15][CH:16]=O.C(=O)([O-])O.[Na+]>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]2[S:13][CH:15]=[CH:16][N:12]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 27773372-(4-Nitrophenyl)thioacetamide

Product 1

HCID 692104452-(4-Nitrobenzyl)-1,3-thiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(4-nitrophenyl)ethanethioamide (0.80 g), chloroacetaldehyde (40% aqueous solution, 2.88 g) and ethanol (20 mL) was heated under reflux for 15 hrs. Saturated aqueous sodium hydrogen carbonate was added to 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, and 2-(4-nitrobenzyl)-1,3-thiazole was obtained as an orange oil (0.35 g, yield 39%) from a fraction eluted with hexane-ethyl acetate (9:1-2:1, v/v).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 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-5c45fcf8d5304f46b253f21eedc39957
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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