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

HRID 35921

반응식

HRID 35921 반응식
[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

참가 물질

4

반응물 2

HCID 66111Trimethylsilylacetylene2회HCID 110736914-(Azidomethyl)benzonitrile

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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 1.20° 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°.

후처리

  1. temperatureonce again refluxed for 3 hours at 1.20°
  2. concentrationthe mixture is concentrated under vacuum

출처 및 근거

ORD 기록
ord-f0035496a7e54c9f94767f9f6a0c8d04
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411982

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