Water → 2-Methylamino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

HRID 1112046Notes

Reaction equation

HRID 1112046 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)=[O:6].[CH3:19][NH:20][C:21]([NH2:23])=[S:22].O>C(O)C>[CH3:19][NH:20][C:21]1[S:22][CH:2]=[C:3]([CH2:4][C:5](=[O:6])[NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[N:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2723704MethylthioureaHCID 223476964-Bromo-3'-trifluoromethylacetoacetanilide

Product 1

HCID 213211582-Methylamino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazoleYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution containing 32.4 g (0.10 mole) of 4-bromo-3'-trifluoromethylacetoacetanilide and 11.3 g (0.13 mole) of N-methylthiourea in 250 ml of ethanol was refluxed for four hours. The reaction mixture was poured into 700 ml of water and ethanol was added. A small quantity of insoluble material was removed by filtration and the filtrate was made strongly alkaline by the addition of ammonium hydroxide. The solution was cooled and an additional 400 ml of water was added. The precipitated solid was collected and dried in an oven. There was obtained 25.5 g (81%) of product, m.p. 153°-55°, N.M.R. (dimethyl-d6 sulfoxide) ∂ 2.8-2.9 (CH3, doublet), 3.5 (CH2), 6.3 (hetero-aromatic), 7.3-8.1 (aromatic, NH), 10.4 (HNC=O).

Workup

  1. temperaturewas refluxed for four hours
  2. additionwas added
  3. customA small quantity of insoluble material was removed by filtration
  4. additionby the addition of ammonium hydroxide
  5. temperatureThe solution was cooled
  6. additionan additional 400 ml of water was added
  7. customThe precipitated solid was collected
  8. customdried in an oven

Sources & evidence

ORD record
ord-c9738e3ca1054aac841276f060f9a533
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

Loading…