p-Xylyl bromide → HCID 14033034, compound

HRID 1194715Notes

Reaction equation

HRID 1194715 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+].[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].[Na].[N-]=[N+]=[N-]>C(O)C>[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]2[C:14]([NH2:15])=[C:16]([C:17]([NH2:19])=[O:18])[N:12]=[N:11]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 7721p-Xylyl bromideHCID 7898CyanoacetamideHCID 33557Sodium AzideHCID 33558AzideHCID 5360545Sodium

Product 1

HCID 14033034HCID 14033034, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A stirred mixture of 4-methylbenzyl bromide (1.3 g, 7.0 mmol) and sodium azide (754 mg, 11.6 mmol) in ethanol (8 ml) was refluxed under a nitrogen atmosphere for 3 hours, cooled to ambient temperature, and filtered. Separately, 2-cyanoacetamide (588 mg, 7.0 mmol) was added to a stirred, refluxing solution of sodium (167 mg, 7 2 mmol) in ethanol (15 ml), followed by dropwise addition of the above azide solution over 20 min. The resulting slurry was refluxed 1 hour, cooled to ambient temperature, and refrigerated. The precipitate was collected by filtration, washed with ethanol, and dried under vacuum to provide 1.12 g (69%) of 1-(4-methylbenzyl)5-amino-1,2,3-triazole-4-carboxamide, m.p. 223°-225° C.

Workup

  1. temperaturewas refluxed under a nitrogen atmosphere for 3 hours
  2. filtrationfiltered
  3. temperatureThe resulting slurry was refluxed 1 hour
  4. temperaturecooled to ambient temperature
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with ethanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e3da4abd77d94e0e8c905de5d10f7769
Source dataset
uspto-grants-1989_03
Patent number
US04816469

Reaction notes

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