Thionyl Chloride → HCID 178509689, compound

HRID 1198171Notes

Reaction equation

HRID 1198171 reaction equation
O[C:2]1([CH:8]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[C:9]2[N:13]=[CH:12][NH:11][N:10]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.S(Cl)(Cl)=O>ClCCl>[C:2]1(=[C:8]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)[C:9]2[N:13]=[CH:12][NH:11][N:10]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178509719HCID 178509719, compound

Product 1

HCID 178509689HCID 178509689, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.24 g of crude 4-[1-hydroxycyclohex-1-yl-1-(1,2,4-triazolyl)methyl]benzonitrile is dissolved at 0° in 50 ml of dichloromethane and stirred for 1 hour at 0° with 22.7 ml of thionyl chloride. Then the mixture is concentrated to dryness under vacuum, dissolved in 50 ml of dichloromethane, stirred with 30 ml of triethylamine for 2 hours, 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, yielding 1.45 g of 4-[1-cyclohexylidene-1-(1,2,4-triazolyl)methyl]benzonitrile as a free base, mp 92°-93°.

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-a3b39be503474f9baad8d53e8ad94fd1
Source dataset
uspto-grants-1994_01
Patent number
US05280035

Reaction notes

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