Acetonitrile → Ethyl 2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 1975252Notes

Reaction equation

HRID 1975252 reaction equation
[C:1]([NH2:4])(=[S:3])[CH3:2].C(#N)C.Cl[CH:9]([C:15]([C:17]([F:20])([F:19])[F:18])=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].C(N(CC)CC)C>>[CH3:2][C:1]1[S:3][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:15]([C:17]([F:18])([F:20])[F:19])[N:4]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 2723949ThioacetamideHCID 2737165Ethyl 2-chloro-4,4,4-trifluoro-3-oxobutanoate

Product 1

HCID 1486077Ethyl 2-methyl-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Conditions

Temperature
76 °C

Procedure

A solution of thioacetamide in acetonitrile (6.66 mol), prepared as in Example 1, is placed in a flask. Ethyl 2-chloro-4,4,4-trifluoroacetoacetate (5.06 mol) is added and an exotherm is observed. Triethylamine (13.64 mol) is added and the mixture is heated to reflux (approx. 76° C.) for one hour. The resulting solution is cooled. Ethyl 2-methyl-4-(trifluoromethyl)-thiazole-5-carboxylate may be isolated by standard means.

Workup

  1. customis placed in a flask
  2. temperaturethe mixture is heated
  3. temperatureThe resulting solution is cooled

Sources & evidence

ORD record
ord-5b1b2afce5314600b8e122f70864cfbe
Source dataset
uspto-grants-1994_02
Patent number
US05284974

Reaction notes

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