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

HRID 1198179Notes

Reaction equation

HRID 1198179 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-70c2bd9a15d5498595193f5fd13241d4
Source dataset
uspto-grants-1994_01
Patent number
US05280035

Reaction notes

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