Aniline → 1-phenyl-1H-1,2,4-triazol-3-amine

HRID 2063651Notes

Reaction equation

HRID 2063651 reaction equation
C1([C:7]2O[N:10]=[C:9]([NH2:12])[N:8]=2)C=CC=CC=1.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:14]1([N:13]2[CH:7]=[N:8][C:9]([NH2:12])=[N:10]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 23054465-Phenyl-1,2,4-oxadiazol-3-amine

Product 1

HCID 218217441-phenyl-1H-1,2,4-triazol-3-amineYield 87%

Procedure

This compound was prepared from 5-phenyl-[1,2,4]oxadiazol-3-ylamine (Journal of Organic Chemistry 28, 1812 (1963) and aniline, via the rearrangement described by Ruccia et al., Journal of Heterocyclic Chemistry 8, 137 (1971). The title compound was isolated as a slightly brownish solid in a yield of 87%. MS ISP (m/e): 161.2 (100) [(M+H)+].

Sources & evidence

ORD record
ord-b489db41bb9b418ba091df64ab8fc0b1
Source dataset
uspto-grants-2012_10
Patent number
US08288403B2

Reaction notes

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