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

HRID 1112045Notes

Reaction equation

HRID 1112045 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=O).

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-0f6b4f41c2e54c1c980280a1b52458df
Source dataset
uspto-grants-1978_10
Patent number
US04120690

Reaction notes

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