Ethyl (chloroformyl)acetate → Ethyl 2-(trifluoromethyl)-1,3-thiazole-5-carboxylate

HRID 1087100

Reaction equation

HRID 1087100 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[S:4].Cl[CH:9]([CH:15]=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11]>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]1[S:4][C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:15][N:5]=1

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetateHCID 4425751Trifluoroethanethioamide

Product 1

HCID 15171126Ethyl 2-(trifluoromethyl)-1,3-thiazole-5-carboxylateYield 24.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 11.22g of 2,2,2,-trifluorothioacetamide and 10.14g of ethyl 2-chloro-2-formylacetate was stirred for 30 minutes in an oil bath of 70° C. and then for 1.5 hours in an oil bath of 100° C., to which 100ml of dichloromethane were added. After removing an insoluble substance, the mixture was concentrated and the residue was subjected to a column chromatography [developing solvent: hexane-ethyl acetate (10:1)], to obtain 3.74g of ethyl 2-(trifluoromethyl)-5-thiazolecarboxylate as yellow liquid.

Workup

  1. waitfor 1.5 hours in an oil bath of 100° C.
  2. customAfter removing an insoluble substance
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-948b288d5fdb46548c04ba9b5338c401
Source dataset
uspto-grants-1991_07
Patent number
US05034404

Linked notes

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