Ethanol → HCID 178513861, compound

HRID 1288306Notes

Reaction equation

HRID 1288306 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[NH:11][N:10]=[N:9][C:8]=1[C:12](=[O:14])[NH2:13].C(O)C.[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:18]([NH:6][C:7]1[NH:11][N:10]=[N:9][C:8]=1[C:12](=[O:14])[NH2:13])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 7412Benzoyl chlorideHCID 178513860HCID 178513860, compound

Product 1

HCID 178513861HCID 178513861, compound

Procedure

Concentrated sulphuric acid (1.5 ml.) was added dropwise, under anhydrous conditions, to an ice-cooled, stirred suspension of 5-amino-4-carbamoyl-1H-1,2,3-triazole (1.27 g.) in benzoyl chloride (15 ml.), and the reaction mixture then stirred at room temperature overnight. The mixture was poured into ice-water, whereupon a gummy precipitate was formed. The aqueous solution was decanted off, and the gum triturated thoroughly with diethyl ether. The remaining solid was then filtered off, and washed well with diethyl ether, to give crude 5-benzamido-4-carbamoyl-1H-1,2,3-triazole (2.26 g.), m.p. 280° C. (with decomposition). An aliquot was heated in boiling ethanol, and the solid filtered off, while still hot, to give pure 5-benzamido-4-carbamoyl-1H-1,2,3-triazole, m.p. 306° C. (with decomposition).

Workup

  1. temperaturecooled
  2. stirringthe reaction mixture then stirred at room temperature overnight
  3. customwas formed
  4. customThe aqueous solution was decanted off
  5. customthe gum triturated thoroughly with diethyl ether
  6. filtrationThe remaining solid was then filtered off
  7. washwashed well with diethyl ether
  8. customto give crude 5-benzamido-4-carbamoyl-1H-1,2,3-triazole (2.26 g.), m.p. 280° C. (with decomposition)
  9. temperatureAn aliquot was heated
  10. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-491b3e8aaaba4ca9a480c4da4cd6a59c
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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