Thionyl Chloride → HCID 178509690, compound

HRID 35918

Reaction equation

HRID 35918 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[N:14]=[CH:13][NH:12][N:11]=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[N:14]=[CH:13][NH:12][N:11]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178509720HCID 178509720, compound

Product 1

HCID 178509690HCID 178509690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7 g of crude 4-[1-hydroxycyclohept-1-yl-1(1,2,4-triazolyl)methyl]benzonitrile is dissolved in 50 ml of dichloromethane at 0° and stirred with 20 ml of thionyl chloride for 1 hour at 0°. Then the mixture is concentrated to dryness under an oil pump vacuum, dissolved in 50 ml of dichloromethane, stirred for 2 hours with 30 ml of triethylamine, diluted with water, extracted three times with ethyl acetate, washed with sodium chloride solution, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, thus producing 1.9 g of 4-di-cycloheptylidene-1-(1,2,4triazolyl)methyl]benzonitrile as the free base, mp 79°-80°.

Workup

  1. concentrationThen the mixture is concentrated to dryness under an oil pump vacuum
  2. dissolutiondissolved in 50 ml of dichloromethane
  3. additiondiluted with water
  4. extractionextracted three times with ethyl acetate
  5. washwashed with sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under vacuum
  8. customchromatographed on silica gel with hexane/ethyl acetate
  9. customthus producing 1.9 g of 4-di-cycloheptylidene-1-(1,2,4triazolyl)methyl]benzonitrile as the free base, mp 79°-80°

Sources & evidence

ORD record
ord-e12fcec478b04c62baf5bd535e7bea4a
Source dataset
uspto-grants-1995_05
Patent number
US05411982

Linked notes

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