Difluoroacetic acid → 5-(Difluoromethyl)-2-methyl-1H-1,2,4-triazol-3(2H)-one

HRID 1883631Notes

Reaction equation

HRID 1883631 reaction equation
[CH3:1][N:2]([C:4]([NH2:6])=[O:5])[NH2:3].[F:7][CH:8]([F:12])[C:9](O)=O>C1(C)C=CC=CC=1>[F:7][CH:8]([F:12])[C:9]1[NH:6][C:4](=[O:5])[N:2]([CH3:1])[N:3]=1

Participants

4

Procedure

20 ml of toluene was added to 500 mg (5.61 mmol) of 2-methyl semicarbazide (produced in the same manner as in Reference Production Example 6), and to this mixture was added 808 mg (8.41 mmol) of difluoroacetic acid, and the mixture was stirred for 10 hours under reflux with heating. The reaction solution was cooled to room temperature, then, concentrated, and the residue was subjected to silica gel thin layer chromatography (eluant: chloroform/methanol=9/1 (v/v)), to obtain 305 mg of 5-difluoromethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one having a melting point of 141.2° C. in the form of colorless solid.

Workup

  1. customproduced in the same manner as in Reference Production Example 6), and to this mixture
  2. temperatureunder reflux
  3. temperaturewith heating
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3f91772aa29f4698bb85bbd7507a48da
Source dataset
uspto-grants-2004_07
Patent number
US06762197B2

Reaction notes

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