Acetic Acid → HCID 13649666, compound

HRID 280671Notes

Reaction equation

HRID 280671 reaction equation
C[O-].[Na+].[C:4]([CH2:6][C:7]([NH2:9])=[O:8])#[N:5].[Cl:10][C:11]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:12]=1[C:13]([C:15]1[CH:24]=[CH:23][C:18]([CH2:19][N:20]=[N+:21]=[N-:22])=[CH:17][CH:16]=1)=[O:14].C(O)(=O)C>C(O)C>[NH2:5][C:4]1[N:20]([CH2:19][C:18]2[CH:17]=[CH:16][C:15]([C:13](=[O:14])[C:12]3[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:11]=3[Cl:10])=[CH:24][CH:23]=2)[N:21]=[N:22][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 10942334Sodium MethoxideHCID 13649663HCID 13649663, compound

Product 1

HCID 13649666HCID 13649666, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred, 65° C. mixture of sodium methoxide (330 mg, 6.11 mmol) in absolute ethanol (20 ml) was treated with 2-cyanoacetamide (527 mg, 6.27 mmol) and kept 10 minutes. The resulting suspension was treated with 4-(2,6-dichlorobenzoyl)benzyl azide (1.6 g, 5.2 mmol), refluxed 2 hours, cooled, treated with glacial acetic acid (600 μl, 629 mg, 10.5 mmol), and evaporated to dryness under vacuum. The residue was chromatographed on a column of silica gel (100 g) eluted with 19:1 (v/v) dichloromethane-methanol to provide 100 mg (5%) 5-amino-1-(4-[2,6-dichlorobenzoyl]benzyl)-1,2,3-triazole-4-carboxamide, m.p. 165°-167° C.

Workup

  1. temperaturerefluxed 2 hours
  2. temperaturecooled
  3. customevaporated to dryness under vacuum
  4. customThe residue was chromatographed on a column of silica gel (100 g)
  5. washeluted with 19:1 (v/v) dichloromethane-methanol

Sources & evidence

ORD record
ord-688200167cb442d8b82225025a26b0a0
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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