Cyanoacetamide → HCID 13649665, compound

HRID 280644Notes

Reaction equation

HRID 280644 reaction equation
[Na].[C:2]([CH2:4][C:5]([NH2:7])=[O:6])#[N:3].[Cl:8][C:9]1[CH:27]=[CH:26][C:12]([C:13]([C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=2[Cl:25])[CH2:18][N:19]=[N+:20]=[N-:21])=[O:14])=[CH:11][CH:10]=1>C(O)C>[NH2:3][C:2]1[N:19]([CH2:18][C:17]2[CH:22]=[CH:23][C:24]([Cl:25])=[C:15]([C:13](=[O:14])[C:12]3[CH:26]=[CH:27][C:9]([Cl:8])=[CH:10][CH:11]=3)[CH:16]=2)[N:20]=[N:21][C:4]=1[C:5]([NH2:7])=[O:6]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 5360545SodiumHCID 15065217HCID 15065217, compound

Product 1

HCID 13649665HCID 13649665, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of sodium (0.147 g, 6.41 mmol) in ethanol (20 ml) under nitrogen atmosphere was added 2-cyanoacetamide (539 mg, 6.41 mmol) and the mixture was refluxed 10 minutes. The mixture was cooled slightly, 3-(4-chlorobenzoyl)-4-chlorobenzyl azide (1.51 g, 4.93 mmol) was added, and the mixture was refluxed 1 hour. The mixture was cooled to 0° C. and filtered. The product was washed with ice cold ethanol (2×5 ml), water (3×5 ml), ice cold ethanol (2×5 ml), and diethyl ether (10 ml), and dried at 50° C. for 3 hours under vacuum to provide 1.16 g (60%) of 5-amino-1-(3-[4-chlorobenzoyl]-4-chlorobenzyl)-1,2,3-triazole-4-carboxamide, m.p. 189°-192° C.

Workup

  1. temperaturethe mixture was refluxed 10 minutes
  2. temperatureThe mixture was cooled slightly
  3. temperaturethe mixture was refluxed 1 hour
  4. filtrationfiltered
  5. washThe product was washed with ice cold ethanol (2×5 ml), water (3×5 ml), ice cold ethanol (2×5 ml), and diethyl ether (10 ml)
  6. customdried at 50° C. for 3 hours under vacuum

Sources & evidence

ORD record
ord-70e07a0ce3a3461da0a6d7998eb15692
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

Loading…