4-Amino-1,2,4-triazole → 1-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

HRID 726803Notes

Reaction equation

HRID 726803 reaction equation
N[N:2]1[CH:6]=[N:5][N:4]=[CH:3]1.Cl[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[F:18])=[O:10]>>[N:5]1([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[O:10])[CH:6]=[N:2][CH:3]=[N:4]1

Participants

3

Reactant 2

HCID 114324-Amino-1,2,4-triazoleHCID 5880832-Chloro-1-(2,4-difluorophenyl)ethanone

Product 1

HCID 5880801-(2,4-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

Procedure

A process for preparing fluconazole, including the steps of (1) acylating 1,3-difluorobenzene (DFB) to obtain 2-chloro-2',4'-difluoroacetophenone (CAP); (2) alkylating 4-amino-4H-1,2,4-triazole (4-AT) with CAP to obtain 2-(1H-1,2,4-triazol-1-yl)-2',4'-difluoroacetophenone (TAAP) salt; (3) deaminating TAAP salt to obtain TAAP; and (4) reacting TAAP with 1,2,4-triazole to obtain fluconazole.

Sources & evidence

ORD record
ord-1eb21e13a93048109cdf037286608238
Source dataset
uspto-grants-1998_01
Patent number
US05710280

Reaction notes

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