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

HRID 1709659노트

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HRID 1709659 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-438730545f2240f78881bb10886f0894
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04950673

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