Trimethylsilylacetylene → 4-[4-Trimethylsilyl-(1,2,3-triazol-1-yl) methyl]benzonitrile

HRID 846085Notes

Reaction equation

HRID 846085 reaction equation
[N:1]([CH2:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=[N+:2]=[N-:3].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[CH3:13][Si:14]([CH3:16])([CH3:15])[C:17]1[N:3]=[N:2][N:1]([CH2:4][C:5]2[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 66111Trimethylsilylacetylene2×HCID 110736914-(Azidomethyl)benzonitrile

Product 1

HCID 191042424-[4-Trimethylsilyl-(1,2,3-triazol-1-yl) methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

38.9 g of 4-azidomethylbenzonitrile is refluxed in 400 ml of toluene with 42 ml of trimethylsilylacetylene for 5 hours at 120°, combined with another 21 ml of trimethylsilylacetylene, and once again refluxed for 3 hours at 120°. Then the mixture is concentrated under vacuum, yielding 63 g of crude 4-[4-trimethylsilyl-(1,2,3-triazol-1-yl)methyl]benzonitrile. The latter is refluxed with a mixture of 700 ml of glacial acetic acid, 380 ml of water, as well as 110 ml of tetrahydrofuran for 2 hours. For working up purposes, the mixture is poured into sodium bicarbonate solution, extracted three times with dichloromethane, washed neutral with water, dried over sodium sulfate, concentrated to dryness under vacuum, and recrystallized from ethyl acetate/hexane, yielding 32.8 g of 4-[1-(1,2,3-triazolyl)methyl]benzonitrile as colorless crystals, mp 83°.

Workup

  1. temperatureonce again refluxed for 3 hours at 120°
  2. concentrationThen the mixture is concentrated under vacuum

Sources & evidence

ORD record
ord-ec64da13b0824bbfa6949fd1b2281c9e
Source dataset
uspto-grants-1992_08
Patent number
US05135937

Reaction notes

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