Sulfuric Acid → 5-acetylamino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide

HRID 414090Notes

Reaction equation

HRID 414090 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:5]=[N:4][C:3]=1[C:15]([NH2:17])=[O:16].[CH3:18][C:19](OC(C)=O)=[O:20].S(=O)(=O)(O)O>C(O)C>[C:19]([NH:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:5]=[N:4][C:3]=1[C:15]([NH2:17])=[O:16])(=[O:20])[CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 28153125-amino-1-[(2-chlorophenyl)methyl]-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 212825985-acetylamino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10,1 g of 5-amino-1-(o-chlorobenzyl)-1H-triazole-4-carboxamide are added, portionwise with stirring, to a mixture of 30,7 g of acetanhydride and 0,1 ml of sulphuric acid and heated to 60° . Stirring is continued for additional 30 minutes at 60° to 70° , the reaction mixture is poored into 250 ml of ethanol, heated to reflux for 30 minutes and evaporated in vacuo to dryness. The residue is triturated with 250 ml of ethyl acetate, the crystalline precipitate is collected and re-crystallised from ethyl acetate yielding 5-acetylamino-1-(o-chlorobenzyl)-1H-1,2,3-triazole-4-carboxamide of m.p. 181°-183°.

Workup

  1. temperatureheated to 60°
  2. temperatureheated
  3. temperatureto reflux for 30 minutes
  4. customevaporated in vacuo to dryness
  5. customThe residue is triturated with 250 ml of ethyl acetate
  6. customthe crystalline precipitate is collected
  7. customre-crystallised from ethyl acetate

Sources & evidence

ORD record
ord-72fec188baa94a90bba1a455e65c2b69
Source dataset
uspto-grants-1988_12
Patent number
US04789680

Reaction notes

Loading…