Hydrochloric Acid → 5-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile

HRID 1848292Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])(=[O:3])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH:21]=[C:22]([Cl:24])[CH:23]=1.C(N(CCCC)CCCC)CCC.Cl>O.C1(C)C=CC=CC=1>[Cl:17][C:18]1[CH:19]=[C:20]([C:25]([OH:30])([C:26]([F:27])([F:28])[F:29])[CH2:2][C:1]([C:4]2[CH:5]=[CH:6][C:7]([N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)=[C:8]([CH:11]=2)[C:9]#[N:10])=[O:3])[CH:21]=[C:22]([Cl:24])[CH:23]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1.00 g (4.71 mmol) of 5-acetyl-2-(1H-1,2,4-triazol-1-yl)benzonitrile, 1.15 g (4.71 mmol) of 3′,5′-dichloro-2,2,2-trifluoroacetophenone, 2.30 g of toluene and 0.26 g (1.41 mmol) of tributylamine were fed and the mixture was stirred for 24 hours at 60° C. The mixture was cooled to room temperature, and a separation operation was performed by adding 20 ml of toluene and an aqueous solution prepared with 0.15 g (1.41 mmol) of 35% hydrochloric acid and 10 ml of water. The toluene phase was washed with 10 ml of water. After removing the solvent by distilling under reduced pressure, the residue was purified by silica gel column chromatography to obtain 1.20 g of 5-(3-(3,5-dichlorophenyl)-4,4,4-trifluoro-3-hydroxybutanoyl)-2-(1H-1,2,4-triazol-1-yl)benzonitrile (yield 56.0%).

Workup

temperatureThe mixture was cooled to room temperature
washThe toluene phase was washed with 10 ml of water
customAfter removing the solvent
distillationby distilling under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-a7b183468bc04763b64a53d93dc68d98
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952175B2

Reaction notes

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