Azidobenzene → 1-Phenyl-4-acryloyloxymethyl-triazole

HRID 1645197

反応式

HRID 1645197 の反応式
[C:1]([O:5][CH2:6][C:7]#[CH:8])(=[O:4])[CH:2]=[CH2:3].[C:9]1([N:15]=[N+:16]=[N-:17])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C.O>[C:9]1([N:15]2[CH:8]=[C:7]([CH2:6][O:5][C:1](=[O:4])[CH:2]=[CH2:3])[N:17]=[N:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 2

HCID 69319AzidobenzeneHCID 82655Propargyl acrylate

生成物 1

HCID 577722581-Phenyl-4-acryloyloxymethyl-triazole収率 89%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Propargyl acrylate (13.5 g, moles), phenyl azide (12.5 g, moles) and tetrakis(acetonitrile)copper (I) hexafluorophosphate (0.84 g, 2.3 mmoles) are dissolved in DMF (100 ml) and stirred at room temperature under nitrogen for 24 hours. The reaction mixture is poured in water and the product is extracted with ethyl acetate. The solvent is distilled under reduced pressure, and mixed with diethyl ether wherefrom the product crystallized as an off-white, crystalline solid (23 g; yield 89%; mp 55-56° C.). 1H NMR (CDCl3, δ ppm) 8.08 (s, 1H), 7.72 (d, 2H), 7.51 (t, 2H), 7.44 (q, qH), 6.48 (d, 1H), 6.17 (q, 1H), 5.88 (d, 1H), 5.50 (s, 2H). 13C NMR (CDCl3, δ ppm) 165.9, 143.4, 136.8, 131.5, 129.7, 128.8, 127.8, 122.1, 120.5, 57.5.

後処理

  1. extractionthe product is extracted with ethyl acetate
  2. distillationThe solvent is distilled under reduced pressure
  3. additionmixed with diethyl ether wherefrom the product
  4. customcrystallized as an off-white, crystalline solid (23 g; yield 89%; mp 55-56° C.)

出典と根拠

ORDレコード
ord-ae5f092d18ea4521940072c951c7de78
出典データセット
uspto-grants-2012_02
特許番号
US08124701B2

関連ノート

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