Chloroform → 3-Biphenyl-4-yl-5-chloromethyl-4-(2-fluorophenyl)-4H-1,2,4-triazole

HRID 1797121

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

[5-Biphenyl-4-yl-4-(2-fluorophenyl)-4H-1,2,4-triazol-3-yl]methanol (1.81 g) was suspended in toluene (25 ml), followed by addition of thionyl chloride (1.5 ml) and chloroform (25 ml), and stirred at 60° C. for 5 hours. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the reaction solution, which was washed with saturated aqueous sodium hydrogen carbonate solution. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The resulting white solid was washed with a mixture solution of n-hexane and ethyl acetate, to afford the entitled compound as white solid (1.54 g, 81%). The physico-chemical values are as follows.

Workup

concentrationAfter the reaction solution was concentrated under reduced pressure, ethyl acetate
additionwas added to the reaction solution, which
washwas washed with saturated aqueous sodium hydrogen carbonate solution
dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
washThe resulting white solid was washed with a mixture solution of n-hexane and ethyl acetate

Sources & evidence

ORD record: ord-aa8a209ba8ae4621b4fb40234d38261a
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07034047B2

Linked notes

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