Thionyl Chloride → HCID 178509686, compound

HRID 1198183Notes

Reaction equation

HRID 1198183 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:9]=[N:10][NH:11][CH:12]=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:9]=[N:10][NH:11][CH:12]=2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178509701HCID 178509701, compound

Product 1

HCID 178509686HCID 178509686, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.1 g of crude 4-[1-hydroxycyclopent-1-yl-1-(1,2,3-triazolyl)methyl]benzonitrile is dissolved at 0° in 50 ml of dichloromethane and stirred with 24 ml of thionyl chloride for 1 hour at 0°. Then the mixture is concentrated to dryness under vacuum, dissolved in 50 ml of dichloromethane, stirred with 32 ml of triethylamine for 2 hours, diluted with water, extracted three times with ethyl acetate, washed with water, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, yielding 2.1 g of 4-[1-cyclopentylidene-1-(1,2,3-triazolyl)methyl]benzonitrile as the tree base, 108°-109° C.

Workup

  1. concentrationThen the mixture is concentrated to dryness under vacuum
  2. dissolutiondissolved in 50 ml of dichloromethane
  3. additiondiluted with water
  4. extractionextracted three times with ethyl acetate
  5. washwashed with water
  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-c0da0c7058894e39a055849ba152aca1
Source dataset
uspto-grants-1994_01
Patent number
US05280035

Reaction notes

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