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

HRID 261753Notes

Reaction equation

HRID 261753 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.Cl[C:22]([O:24]C)=[O:23].O.N1C=CC=C[CH:28]=1>>[C:22]([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)(=[O:23])[CH3:28]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6586Methyl chloroformateHCID 213211472-Amino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

Product 1

HCID 213211532-Acetoxyamino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole

Procedure

To a solution of 5.0 g (0.017 mole) of 2-amino-4-(3-trifluoromethylphenylcarbamoylmethyl)thiazole in 22 ml of pyridine, there was added dropwise 2.8 g (0.03 mole) of methyl chloroformate. The solution was stirred and heated at 40°-45° for eighteen hours. The mixture was poured into 300 ml of cold water and stirring induced crystal formation. The solid was collected and the filter cake was washed with water. There was obtained 4.9 g of product, m.p. 137°-40°. N.M.R. (dimethyl-d6 sulfoxide) ∂ 3.6-3.9 (OCH3, CH2), 6.8 (hetero-aromatic), 7.3-8.1 (aromatic), 10.4 (HNC=0).

Workup

  1. temperatureheated at 40°-45° for eighteen hours
  2. stirringstirring induced crystal formation
  3. customThe solid was collected
  4. washthe filter cake was washed with water

Sources & evidence

ORD record
ord-1e828202ae4f45889f1709b9c0fa476a
Source dataset
uspto-grants-1979_05
Patent number
US04152329

Reaction notes

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