Thionyl Chloride → HCID 178509687, compound

HRID 846080

Reaction equation

HRID 846080 reaction equation
O[C:2]1([CH:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[C:8]2[N:12]=[CH:11][NH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O>ClCCl>[C:2]1(=[C:7]([C:13]2[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=2)[C:8]2[N:12]=[CH:11][NH:10][N:9]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178509718HCID 178509718, compound

Product 1

HCID 178509687HCID 178509687, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.21 g of crude 4-[1-hydroxycyclopent-1-yl-1-(1,2,4-triazolyl)methyl]benzonitrile is dissolved in 50 ml of dichloromethane at 0° and stirred at 0° with 24 ml of thionyl chloride for 1 hour. Then the mixture is concentrated to dryness under vacuum, dissolved in 50 ml of dichloromethane, stirred for 2 hours with 32 ml of triethylamine, diluted with water, extracted four 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 obtaining 2.1 g of 4-[1-cyclopentylidene-1-(1,2,4triazolyl)methyl]benzonitrile as the free base, mp 72°.

Workup

  1. concentrationThen the mixture is concentrated to dryness under vacuum
  2. dissolutiondissolved in 50 ml of dichloromethane
  3. additiondiluted with water
  4. extractionextracted four 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

Sources & evidence

ORD record
ord-620ec205623e4e77a22824447a891f7d
Source dataset
uspto-grants-1992_08
Patent number
US05135937

Linked notes

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