Thiourea → 2-amino-4-[N-4-chlorophenyl-N-methyl(carbamoylmethyl)] thiazole

HRID 224495Notes

Reaction equation

HRID 224495 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]([N:7]([CH3:15])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=[O:6].[NH2:17][C:18]([NH2:20])=[S:19]>C(O)C>[NH2:20][C:18]1[S:19][CH:2]=[C:3]([CH2:4][C:5](=[O:6])[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[CH3:15])[N:17]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 202975284-bromo-4'-chloro-N-methylacetoacetanilide

Product 1

HCID 544847172-amino-4-[N-4-chlorophenyl-N-methyl(carbamoylmethyl)] thiazoleYield 66.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 ml reaction flask equipped with a condenser, magnetic stirrer, thermometer and heating mantle was charged with 20.2 g (0.066 mole) of 4-bromo-4'-chloro-N-methylacetoacetanilide, 200 ml of ethanol and 5.4 g (0.071 mole) of thiourea. The reaction solution was refluxed for three hours. After cooling, about one-half of the solvent was removed on the rotary evaporator and the solution was poured into 300 ml of water. After adding sufficient ammonium hydroxide to pH 8, additional water was added. The precipitated crystalline product was dried in a vacuum oven. There was obtained 12.4 g (66.7%) of white material, M.P. 148°-50°. N.M.R. (dimethyl-d6 sulfoxide, CDCl3) ∂3.2 (NCH3), 3.3 (CH2), 6.0 (heteroaromatic), 7.3-7.5 (aromatic).

Workup

  1. customA 500 ml reaction flask
  2. customequipped with a condenser, magnetic stirrer
  3. temperaturethermometer and heating mantle
  4. temperatureThe reaction solution was refluxed for three hours
  5. temperatureAfter cooling, about one-half of the solvent
  6. customwas removed on the rotary evaporator
  7. additionthe solution was poured into 300 ml of water
  8. additionAfter adding sufficient ammonium hydroxide to pH 8, additional water
  9. additionwas added
  10. customThe precipitated crystalline product was dried in a vacuum oven

Sources & evidence

ORD record
ord-445ca06c839241da95e1f6d382f94a2a
Source dataset
uspto-grants-1980_11
Patent number
US04232163

Reaction notes

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