Cyanoacetamide → HCID 13649673, compound

HRID 280664Notes

Reaction equation

HRID 280664 reaction equation
[Na].[C:2]([CH2:4][C:5]([NH2:7])=[O:6])#[N:3].[C:8]([C:16]1[CH:25]=[CH:24][C:19]([CH2:20][N:21]=[N+:22]=[N-:23])=[CH:18][C:17]=1[CH3:26])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(C1C=CC(C)=CC=1CN=[N+]=[N-])(=O)C1C=CC=CC=1>C(O)C>[NH2:3][C:2]1[N:21]([CH2:20][C:19]2[CH:24]=[CH:25][C:16]([C:8](=[O:15])[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[C:17]([CH3:26])[CH:18]=2)[N:22]=[N:23][C:4]=1[C:5]([NH2:7])=[O:6]

Participants

6

Reactant 4

HCID 7898CyanoacetamideHCID 5360545SodiumHCID 23320948HCID 23320948, compoundHCID 23320974HCID 23320974, compound

Product 1

HCID 13649673HCID 13649673, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred solution of sodium (104 mg, 4.50 mmol) in absolute ethanol at 60° C. was treated with 2-cyanoacetamide (378 mg, 4.50 mmol), kept 5 min, and treated with a solution of 942 mg of a 4:1 mixture of 4-benzoyl-3-methyl-benzyl azide and 2-benzoyl-5-methylbenzyl azide in absolute ethanol (6 ml). The mixture was refluxed 1 hour, cooled to 0° , and filtered. The solid was washed twice with water, acidified with acetic acid, and dried. The ethanol filtrate was acidified with acetic acid and evaporated to dryness at 40° C. under vacuum. The residue from the filtrate was combined with the above solid and chromatographed on a column of silica gel (125 g) eluted in 17 ml fractions with 19:1 (v/v) dichloromethane-methanol. Fractions 19-25 were combined and evaporated to dryness, and the residue was triturated with diethyl ether (3×10 ml). The remaining solid was dried 18 hours at ambient temperature under vacuum to provide 330 mg (31%) 5-amino-1-(4-benzoyl-3-methylbenzyl)-1,2,3-triazole4-carboxamide, m.p. 181°-182° C.

Workup

  1. temperatureThe mixture was refluxed 1 hour
  2. temperaturecooled to 0°
  3. filtrationfiltered
  4. washThe solid was washed twice with water
  5. customdried
  6. customevaporated to dryness at 40° C. under vacuum
  7. customchromatographed on a column of silica gel (125 g)
  8. washeluted in 17 ml fractions with 19:1 (v/v) dichloromethane-methanol
  9. customevaporated to dryness
  10. customthe residue was triturated with diethyl ether (3×10 ml)
  11. customThe remaining solid was dried 18 hours at ambient temperature under vacuum

Sources & evidence

ORD record
ord-7538825f6c6940f1aca6497a2bd8d9be
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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