Hydrogen Peroxide → HCID 13649672, compound

HRID 280663Notes

Reaction equation

[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[C:12]([Cl:14])[C:11]([S:15][C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:10]([Cl:23])[CH:9]=2)[N:5]=[N:4][C:3]=1[C:24]([NH2:26])=[O:25].FC(F)(F)C(O)=[O:30].OO.[OH-].[Na+]>C(O)(=O)C.O.C(OCC)C>[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[C:12]([Cl:14])[C:11]([S:15]([C:16]3[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=3)=[O:30])=[C:10]([Cl:23])[CH:9]=2)[N:5]=[N:4][C:3]=1[C:24]([NH2:26])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A stirred solution of 5-amino-1-(4-[4-chlorophenylthio]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide (176 mg, 0.409 mmol) in glacial acetic acid (10 ml) was treated at ambient temperature with trifluoroacetic acid (94.3 μl, 139 mg, 1.23 mmol) and 30% aqueous hydrogen peroxide (2.72 ml). The mixture was stirred 45 minutes, diluted with glacial acetic acid (3.0 ml), stirred 3.25 hours, and diluted with water (100 ml). The mixture was cooled to 0° C., a small volume of diethyl ether was added, the mixture was carefully basified by addition of 50% (w/v) aqueous sodium hydroxide, and diethyl ether was evaporated under vacuum. The resulting suspension was filtered, and the solid washed well with water and dried at 45° C. under vacuum to provide 173 mg (95%) of 5-amino-1-(4-[4-chlorophenylsulfinyl]-3,5-dichlorobenzyl)-1,2,3-triazole-4-carboxamide. Recrystallization from ethanol provided material of m.p. 195°-197 ° C.

Workup

stirringstirred 3.25 hours
customwas evaporated under vacuum
filtrationThe resulting suspension was filtered
washthe solid washed well with water
customdried at 45° C. under vacuum

Sources & evidence

ORD record: ord-763688de1d504fa895fbce158daf8779
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04590201

Reaction notes

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