Thionyl Chloride → 4-[1-Cycloheptylidene-1(imidazolyl)methyl]benzonitrile

HRID 35910Notes

Reaction equation

HRID 35910 reaction equation
O[C:2]1([CH:9]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O>ClCCl>[C:2]1(=[C:9]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[C:10]2[NH:14][CH:13]=[CH:12][N:11]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 544731204-[1-Hydroxycyclohept-1-yl-1-(imidazolyl)methyl]benzonitrile

Product 1

HCID 544992784-[1-Cycloheptylidene-1(imidazolyl)methyl]benzonitrileYield 21.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0°, 10 g of crude 4-[1-hydroxycyclohept-1-yl-1-(imidazolyl)methyl]benzonitrile is dissolved in 100 ml of dichloromethane and stirred with 10 ml of thionyl chloride for 4 hours. Then the mixture is concentrated to dryness under an oil pump vacuum, taken up in 100 ml of dichloromethane, and stirred with 40 ml of triethylamine for 18 hours at 25°. For working up purposes, the mixture is combined with water, extracted twice with dichloromethane, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, thus producing 2.03 g of 4-[1-cycloheptylidene-1(imidazolyl)methyl]benzonitrile as the oily, free base.

Workup

  1. concentrationThen the mixture is concentrated to dryness under an oil pump vacuum
  2. extractionextracted twice with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness under vacuum
  5. customchromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-671caced308d4361b1c56ba319af25b9
Source dataset
uspto-grants-1995_05
Patent number
US05411982

Reaction notes

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