Ethyl cyanoacetate → Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate

HRID 27686

反応式

HRID 27686 の反応式
[Na].[C:2]1([N:8]=[N+:9]=[N-:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])#[N:12]>C(O)C.O>[NH2:12][C:11]1[N:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[N:10][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

参加物

6

反応物 3

HCID 7764Ethyl cyanoacetateHCID 69319AzidobenzeneHCID 5360545Sodium

生成物 1

HCID 253349Ethyl 5-amino-1-phenyl-1H-1,2,3-triazole-4-carboxylate

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
45 °C

実験手順

A solution of sodium (2.04 g; 0.089 mole) in ethanol (50 ml) was added to a mixture of phenyl azide (11.9 g; 0.1 mole) and ethyl cyanoacetate (11.3 g; 0.1 mole) and the product gently warmed to 45° C. with stirring for 5 mins. After stirring at ambient temperature for a further 15 minutes the flask was immersed in water at room temperature for 3 hrs. A white solid separated which was filtered off after dilution of the mixture with water and washed with water. Recrystallisation from ethanol gave 18.4 g. (79%) of material of mp 124.5-125.5° C. (lit mp 126°; B. R. Brown, D. L. Hammick and S. G. Heritage J. Chem. Soc. 3820 [1953]).

後処理

  1. stirringAfter stirring at ambient temperature for a further 15 minutes the flask
  2. customA white solid separated which
  3. filtrationwas filtered off after dilution of the mixture with water
  4. washwashed with water
  5. customRecrystallisation from ethanol
  6. customgave 18.4 g

出典と根拠

ORDレコード
ord-b3e067cf1f534ffe8363abbafa8f7d65
出典データセット
uspto-grants-1980_09
特許番号
US04223032

関連ノート

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