Water → 1-(4-Fluorophenethyl)-1-(4-chlorophenyl)hydrazine

HRID 1775911Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[F:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17]Br)=[CH:14][CH:13]=1.O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[F:11][C:12]1[CH:20]=[CH:19][C:15]([CH2:16][CH2:17][N:9]([C:6]2[CH:7]=[CH:8][C:3]([Cl:2])=[CH:4][CH:5]=2)[NH2:10])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 77.5 °C

Procedure

The title compound was prepared by General Method 2. 4-chlorophenylhydrazine hydrochloride (2.2 g) was added to a vigorously stirred mixture of tetra-n-butylammonium chloride (200 mg) in 50% aqueous sodium hydroxide (12 mL) followed by 4-fluorophenethyl bromide (2.5 g). The mixture was heated at 75-80° C. (oil bath temp.) for 3.5 h. After cooling to room temperature, water was added and the mixture extracted with chloroform and the chloroform layer was washed with brine. The combined extract was dried (sodium sulfate), evaporated in vacuo to give a dark oil which was chromatographed over silica gel, eluting with chloroform followed by recrystallization from cyclohexane to obtain 750 mg of product.

Workup

temperatureAfter cooling to room temperature
extractionthe mixture extracted with chloroform
washthe chloroform layer was washed with brine
extractionThe combined extract
dry with materialwas dried (sodium sulfate)
customevaporated in vacuo
customto give a dark oil which
customwas chromatographed over silica gel
washeluting with chloroform
customfollowed by recrystallization from cyclohexane

Sources & evidence

ORD record: ord-c633a776f3ce42458aac9364d5e54ff1
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260429B2

Reaction notes

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