Ethyl chloroformate → HCID 22288378, compound

HRID 1296465Notes

Reaction equation

HRID 1296465 reaction equation
CCCCCC.C([Li])CCC.[CH3:12][N:13]1[C:17]([C:18]2[S:19][CH:20]=[CH:21][N:22]=2)=[CH:16][C:15]([C:23]([F:26])([F:25])[F:24])=[N:14]1.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1COCC1>[CH3:12][N:13]1[C:17]([C:18]2[S:19][C:20]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:21][N:22]=2)=[CH:16][C:15]([C:23]([F:26])([F:24])[F:25])=[N:14]1

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 22288373HCID 22288373, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 22288378HCID 22288378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An n-butyl lithium-n-hexane solution (1.6 M) was added to a mixture of 2-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiazole and THF at −50° C. or below, followed by stirring at −50° C. or below for 90 minutes. Ethyl chloroformate was added to the reaction solution at −20° C. or below. After stirring at −20° C. or below for 15 minutes, it was subjected to purification in the usual way to give ethyl 2-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiazole-5-carboxylate. This was hydrolyzed with a base in the usual way to give 2-(1-methyl-3-trifluoromethyl-1H-pyrazol-5-yl)thiazole-5-carboxylic acid.

Workup

  1. stirringAfter stirring at −20° C. or below for 15 minutes
  2. customit was subjected to purification in the usual way

Sources & evidence

ORD record
ord-fa273eb2845b4719a9befb14572beba3
Source dataset
uspto-grants-2007_07
Patent number
US07247635B2

Reaction notes

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