Acetic Acid → 5-Amino-1-(3-chloro-4-[4-chlorobenzoyl]-5-methylbenzyl)-1,2,3-triazole-4-carboxamide

HRID 280676Notes

Reaction equation

HRID 280676 reaction equation
[Na].[C:2]([CH2:4][C:5]([NH2:7])=[O:6])#[N:3].[Cl:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH3:28])[C:18]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)[CH2:12][N:13]=[N+:14]=[N-:15].C(O)(=O)C>C(O)C>[NH2:3][C:2]1[N:13]([CH2:12][C:11]2[CH:16]=[C:17]([CH3:28])[C:18]([C:19](=[O:27])[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)=[C:9]([Cl:8])[CH:10]=2)[N:14]=[N:15][C:4]=1[C:5]([NH2:7])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 5360545SodiumHCID 233209623-Chloro-4-(4-chlorobenzoyl)-5-methylbenzyl azide

Product 1

HCID 136496755-Amino-1-(3-chloro-4-[4-chlorobenzoyl]-5-methylbenzyl)-1,2,3-triazole-4-carboxamideYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred, 60° C. solution of sodium (88.7 mg, 3.84 mmol) in absolute ethanol (9.6 ml) was treated with 2-cyanoacetamide (323 mg, 3.84 mmol), kept 5 min., and treated with 3-chloro-4-(4-chlorobenzoyl)-5-methylbenzyl azide (1.03 g, 3.20 mmol). The mixture was refluxed 1 hour, cooled to ambient temperature, acidified with glacial acetic acid (487 μl, 511 mg, 7.68 mmol), and evaporated to dryness at 30° C. under vacuum. The residue was chromatographed on a column of silica gel (150 g) eluted in 17 ml fractions with 19:1 (v/v) dichloromethane-methanol. Fractions 22-38 were combined and evaporated to dryness. The residual glass was kept 18 hours at ambient temperature with diethyl ether (25 ml), filtered, washed with diethyl ether, and dried to provide 870 mg (67%) crystalline 5-amino-1-(3-chloro-4-[4-chlorobenzoyl]-5-methylbenzyl)-1,2,3-triazole-4 -carboxamide, m.p. 205°-206° C.

Workup

  1. temperatureThe mixture was refluxed 1 hour
  2. customevaporated to dryness at 30° C. under vacuum
  3. customThe residue was chromatographed on a column of silica gel (150 g)
  4. washeluted in 17 ml fractions with 19:1 (v/v) dichloromethane-methanol
  5. customevaporated to dryness
  6. waitThe residual glass was kept 18 hours at ambient temperature with diethyl ether (25 ml)
  7. filtrationfiltered
  8. washwashed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-9b62d756e4a44b1ab9e811dfda3503a7
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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