Cyanoacetamide → HCID 14033028, compound

HRID 2414157Notes

Reaction equation

HRID 2414157 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].[OH-].[Na+].[CH3:9][C:10]1[CH:19]=[CH:18][C:13]([CH2:14][N:15]=[N+:16]=[N-:17])=[CH:12][C:11]=1[C:20]([Cl:24])=[C:21]([Cl:23])[Cl:22]>C(O)C>[NH2:2][C:1]1[N:15]([CH2:14][C:13]2[CH:18]=[CH:19][C:10]([CH3:9])=[C:11]([C:20]([Cl:24])=[C:21]([Cl:23])[Cl:22])[CH:12]=2)[N:16]=[N:17][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 14798Sodium HydroxideHCID 23036214HCID 23036214, compound

Product 1

HCID 14033028HCID 14033028, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a hot (60° C.) solution of cyanoacetamide (1.09 g) in 30 ml of ethanol, 13 ml of a methanolic solution of NaOH (1N) was added and the resulting mixture was stirred at 60° C. for 20 minutes. At this point a solution of 4-methyl-3-(trichlorovinyl)benzyl azide (1.65 g) in 10 ml of ethanol was added and the reaction mixture stirred at 60° C. for an additional two hours. The precipitate was removed by filtration and rinsed with ethanol and ether. The filtrate was diluted with water (200 ml) and the resulting precipitate collected (1.56 g). The crude product was chromatographed on silica with 95:5 methylene chloride:methanol to give 889 mg of 5-amino-1-[4-methyl-3-(trichlorovinyl)benzyl]-1,2,3-triazole-4-carboxamide, m.p. 196°-197° C.

Workup

  1. stirringthe reaction mixture stirred at 60° C. for an additional two hours
  2. customThe precipitate was removed by filtration
  3. washrinsed with ethanol and ether
  4. additionThe filtrate was diluted with water (200 ml)
  5. customthe resulting precipitate collected (1.56 g)
  6. customThe crude product was chromatographed on silica with 95:5 methylene chloride

Sources & evidence

ORD record
ord-4502fa64111d43a68a7f056166dbec04
Source dataset
uspto-grants-1988_01
Patent number
US04721791

Reaction notes

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