Cyanoacetamide → 5-Amino-1-(3,4-dichlorobenzyl)-1,2,3-triazole-4-carboxamide

HRID 1709659ノート

反応式

HRID 1709659 の反応式
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[Na].[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:12][N:13]=[N+:14]=[N-:15]>C(O)C>[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=1[Cl:19])[CH2:12][N:13]1[C:1]([NH2:2])=[C:3]([C:4]([NH2:6])=[O:5])[N:15]=[N:14]1

参加物

5

反応物 3

HCID 7898CyanoacetamideHCID 5360545SodiumHCID 150652184-(Azidomethyl)-1,2-dichlorobenzene

生成物 1

HCID 140330335-Amino-1-(3,4-dichlorobenzyl)-1,2,3-triazole-4-carboxamide収率 67%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

A stirred mixture of 3,4-dichlorobenzyl chloride (12.6 g, 64.5 mmol) and sodium azide (7.0 g, 0.11 mole) in absolute ethanol (70 ml) was refluxed for 4.75 hours, cooled and filtered to provide a solution of 3,4-dichlorobenzyl azide. Separately, 2-cyanoacetamide (5.5 g, 65 mmol) was added to a 35° C. solution of sodium (1.5 g, 65 mmol) in absolute ethanol (125 ml), and to the resulting suspension was added the above azide solution dropwise over 10 minutes. The combined mixtures were refluxed for 1 hour, kept 16 hours at ambient temperature and 1 hour at 5° C., and filtered. The crude product was dried under vacuum, dissolved in boiling ethanol (290 ml), filtered hot, and cooled to 0° C. The solid was collected by filtration and dried under vacuum to provide 12.4 g (67%) of 1-(3,4-dichlorobenzyl)-5-amino-1,2,3-triazole-4-carboxamide, m.p 221°-222° C.

後処理

  1. temperatureThe combined mixtures were refluxed for 1 hour
  2. filtrationfiltered
  3. dry with materialThe crude product was dried under vacuum
  4. dissolutiondissolved
  5. filtrationfiltered hot
  6. filtrationThe solid was collected by filtration
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-438730545f2240f78881bb10886f0894
出典データセット
uspto-grants-1990_08
特許番号
US04950673

反応ノート

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