Water → 2-(1,3-Dimethylureido)-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

HRID 1112047Notes

Reaction equation

HRID 1112047 reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][C:9](=[O:21])[NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]=1.[CH3:22][N:23]=[C:24]=[O:25].O>N1C=CC=CC=1>[CH3:1][N:2]([C:3]1[S:4][CH:5]=[C:6]([CH2:8][C:9](=[O:21])[NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:7]=1)[C:24]([NH:23][CH3:22])=[O:25]

Participants

5

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 213211582-Methylamino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

Product 1

HCID 706026162-(1,3-Dimethylureido)-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazoleYield 47.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution comprising 12.7 g (0.04 mole) of 2-methylamino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole, 3.1 g (0.054 mole) of methyl isocyanate in 40 ml of pyridine was heated at about 45° for 24 hours. The reaction solution was poured into water and the crude product was collected. Two recrystallizations from isopropanol-heptane yielded 7.1 g of desired product, m.p. 125°-27°. N.M.R. (dimethyl-d6 sulfoxide) ∂ 2.8 (CH3, doublet), 3.5 (CH3, singlet), 3.8 (CH2), 6.9 (hetero-aromatic), 7.3-8.1 (aromatic), 10.4 (HNC=O).

Workup

  1. temperaturewas heated at about 45° for 24 hours
  2. customthe crude product was collected
  3. customTwo recrystallizations from isopropanol-heptane

Sources & evidence

ORD record
ord-05d9b22ef26c49ae929a04fe2915d1c6
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

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