4-Amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one → HCID 14677257, compound

HRID 1886503Notes

Reaction equation

[NH2:1][N:2]1[C:6]([CH3:7])=[N:5][NH:4][C:3]1=[O:8].[F:9][C:10]([F:23])([F:22])[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[F:23][C:10]([F:9])([F:22])[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([NH:1][N:2]1[C:6]([CH3:7])=[N:5][NH:4][C:3]1=[O:8])(=[O:20])=[O:19]

Participants

Conditions

Temperature: -10 °C

Procedure

10.0 g (0.088 mol) of 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 50 ml of dry pyridine, the mixture is cooled to -10° C., and 32.7 g (0.12 mol) of 2-trifluoromethoxy-benzenesulphonyl chloride are added. The reaction mixture is allowed to reach room temperature (approximately 20° C.) and stirred for approximately 12 hours. After the mixture has been concentrated, the residue is taken up in methylene chloride and shaken with 1N hydrochloric acid and then with water. The organic phase is dried with sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under a water pump vacuum. 23.1 g (80% of theory) of 4-(2-trifluoromethoxy-phenylsulphonylamino)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are obtained as an oily residue.

Workup

customto reach room temperature
custom(approximately 20° C.)
concentrationAfter the mixture has been concentrated
stirringshaken with 1N hydrochloric acid
dry with materialThe organic phase is dried with sodium sulfate
filtrationfiltered
distillationThe solvent is carefully distilled off from the filtrate under a water pump vacuum

Sources & evidence

ORD record: ord-975dfd56f3f54a8e81d3aeacad428653
Source dataset: uspto-grants-1992_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05151514

Reaction notes

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