Acetic Acid → HCID 13649674, compound

HRID 280673Notes

Reaction equation

HRID 280673 reaction equation
[Na].[C:2]([CH2:4][C:5]([NH2:7])=[O:6])#[N:3].[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([C:13]([C:15]2[C:24]([CH3:25])=[CH:23][C:18]([CH2:19][N:20]=[N+:21]=[N-:22])=[CH:17][C:16]=2[CH3:26])=[O:14])=[CH:11][CH:10]=1.C(O)(=O)C>C(O)C>[NH2:3][C:2]1[N:20]([CH2:19][C:18]2[CH:17]=[C:16]([CH3:26])[C:15]([C:13](=[O:14])[C:12]3[CH:27]=[CH:28][C:9]([Cl:8])=[CH:10][CH:11]=3)=[C:24]([CH3:25])[CH:23]=2)[N:21]=[N:22][C:4]=1[C:5]([NH2:7])=[O:6]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 5360545SodiumHCID 23320965HCID 23320965, compound

Product 1

HCID 13649674HCID 13649674, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred, 60° solution of sodium (105 mg, 4.55 mmol) in absolute ethanol (11.4 ml) was treated in one portion with 2-cyanoacetamide (382 mg, 4.55 mmol), kept 5 minutes, and treated in one portion with a solution of 4-(4-chlorobenzoyl)-3,5-dimethylbenzyl azide (1.05 g, 3.50 mmol) in absolute ethanol (4 ml). The mixture was refluxed 1 hour, cooled to ambient temperature, acidified with glacial acetic acid (577 μl, 605 mg, 9.10 mmol), and evaporated almost to dryness under vacuum. The residue was refluxed briefly with methanol (7 ml), cooled to ambient temperature, and filtered. The solid product was washed four times with small volumes of methanol, washed three times with water, and dried under vacuum at 40° C. to provide 870 mg (65%) 5-amino-1-(4-[4-chlorobenzoyl]-3,5-dimethylbenzyl)-1,2,3-triazole-4-carboxamide, m.p. 208°-209° C.

Workup

  1. temperatureThe mixture was refluxed 1 hour
  2. customevaporated almost to dryness under vacuum
  3. temperatureThe residue was refluxed briefly with methanol (7 ml)
  4. temperaturecooled to ambient temperature
  5. filtrationfiltered
  6. washThe solid product was washed four times with small volumes of methanol
  7. washwashed three times with water
  8. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-0a1f4b6adb2a43f38018f9d39efd149e
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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