Chloroacetaldehyde → 2-[2-(4-Nitrophenyl)ethyl]-1,3-thiazole

HRID 30652

Reaction equation

HRID 30652 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12](=[S:14])[NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:16][CH:17]=O>C(O)(C)(C)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[S:14][CH:16]=[CH:17][N:13]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 826731463-(4-Nitrophenyl)propanethioamide

Product 1

HCID 692092882-[2-(4-Nitrophenyl)ethyl]-1,3-thiazoleYield 28%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 3-(4-nitrophenyl)propanethioamide (1.0 g), chloroacetaldehyde (40% aqueous solution, 2.83 g) and tert-butanol (20 mL) was heated under reflux for 2 hrs. 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 to give 2-[2-(4-nitrophenyl)ethyl]-1,3-thiazole as pale-yellow crystals (0.31 g, yield 28%) from a fraction eluted with hexane-ethyl acetate (3:1, v/v). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 92-93° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hrs
  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-4645e2f336fb42c1ac43af807b1a0cc1
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Linked notes

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