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

HRID 261752Notes

Reaction equation

HRID 261752 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8](=[O:20])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:6]=1.[CH3:21][N:22]=[C:23]=[O:24].O>N1C=CC=CC=1>[CH3:21][NH:22][C:23](=[O:24])[NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8](=[O:20])[NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:17])[F:18])[CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12228Methyl IsocyanateHCID 213211472-Amino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

Product 1

HCID 213211542-(3-Methylureido)-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazoleYield 84.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 10 g (0.033 mole) of 2-amino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole, and 2.3 g (0.04 mole) of methyl isocyanate in 50 ml of pyridine was heated at 50° for three hours. The reaction solution was mixed with 400 ml of water and allowed to stand overnight in the refrigerator. On the following morning, the crystalline solid was collected and dried in the oven. There was obtained 10 g of the desired product, m.p. 200°-203°. N.M.R. (dimethyl-d6 sulfoxide) ∂ 2.7-2.8 (CH3, doublet), 6.8 (hetero-aromatic), 7.3-8.1 (aromatic), 10.4 (HNC=0).

Workup

  1. customOn the following morning, the crystalline solid was collected
  2. customdried in the oven

Sources & evidence

ORD record
ord-38896520bc8343098f8cd8412fc795e4
Source dataset
uspto-grants-1979_05
Patent number
US04152329

Reaction notes

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