Cyanoacetamide → 5-Amino-1-(4-[4-chlorobenzoyl]-3-chlorobenzyl)-1,2,3-triazole-4-carboxamide

HRID 280641Notes

Reaction equation

HRID 280641 reaction equation
[C:1]([CH2:3][C:4]([NH2:6])=[O:5])#[N:2].C[O-].[Na+].[Cl:10][C:11]1[CH:29]=[CH:28][C:14]([C:15]([C:17]2[CH:26]=[CH:25][C:20]([CH2:21][N:22]=[N+:23]=[N-:24])=[CH:19][C:18]=2[Cl:27])=[O:16])=[CH:13][CH:12]=1>C(O)C>[NH2:2][C:1]1[N:22]([CH2:21][C:20]2[CH:25]=[CH:26][C:17]([C:15](=[O:16])[C:14]3[CH:28]=[CH:29][C:11]([Cl:10])=[CH:12][CH:13]=3)=[C:18]([Cl:27])[CH:19]=2)[N:23]=[N:24][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 136496614-(4-Chlorobenzoyl)-3-chlorobenzyl azide

Product 1

HCID 100689495-Amino-1-(4-[4-chlorobenzoyl]-3-chlorobenzyl)-1,2,3-triazole-4-carboxamideYield 32%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred suspension of 2-cyanoacetamide (378 mg, 4.50 mmol) in ethanol (15 ml) was treated with sodium methoxide (236 mg, 4.37 mmol), refluxed 10 minutes, cooled slightly, and treated with 4-(4-chlorobenzoyl)-3-chlorobenzyl azide (1.03 g, 3.36 mmol) dissolved in ethanol (4 ml). The mixture was refluxed 2 hours, cooled to ambient temperature, and filtered. The solids were washed with ethanol, and the combined filtrate and wash were evaporated to dryness under vacuum. The residue was dissolved in 19:1 (v/v) dichloromethane-methanol (40 ml) and chromatographed on a column of silica gel (60 g) eluted in 20 ml fractions with 97:3 (v/v) dichloromethane-methanol. Fractions 15-42 were combined and evaporated under vacuum to provide 402 mg (32%) of 5-amino-1-(4-[4-chlorobenzoyl]-3-chlorobenzyl)-1,2,3-triazole-4-carboxamide, m.p. 203°-205° C.

Workup

  1. temperaturerefluxed 10 minutes
  2. temperaturecooled slightly
  3. temperatureThe mixture was refluxed 2 hours
  4. filtrationfiltered
  5. washThe solids were washed with ethanol
  6. washthe combined filtrate and wash
  7. customwere evaporated to dryness under vacuum
  8. dissolutionThe residue was dissolved in 19:1 (v/v) dichloromethane-methanol (40 ml)
  9. customchromatographed on a column of silica gel (60 g)
  10. washeluted in 20 ml fractions with 97:3 (v/v) dichloromethane-methanol
  11. customevaporated under vacuum

Sources & evidence

ORD record
ord-f9cf472eee214c20add6e68628ce1608
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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