Sulfuric Acid → 5-Benzamido-4-benzoylcarbamoyl-1-benzyl-1,2,3-triazole

HRID 1288294Notes

Reaction equation

HRID 1288294 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]=[N:9][C:8]=1[C:19](=[O:21])[NH2:20].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[C:22]([NH:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]=[N:9][C:8]=1[C:19](=[O:21])[NH:20][C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 7412Benzoyl chlorideHCID 2254355-Amino-1-benzyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 215044225-Benzamido-4-benzoylcarbamoyl-1-benzyl-1,2,3-triazole

Procedure

Concentrated sulphuric acid (1.5 ml.) was added dropwise, under anhydrous conditions, to an ice-cooled, stirred suspension of 5-amino-1benzyl-4-carbamoyl-1,2,3-triazole (2.17 g.; prepared as described by J. R. E. Hoover and A. R. Day, J.Amer.Chem.Soc., 1956, 78, 5832) in benzoyl chloride (24 ml.). Stirring was continued at room temperature overnight. The clear solution which formed was then poured into ice-water, the precipitated solid was filtered off, washed well with water and diethyl ether to give 5-benzamido-4-benzoylcarbamoyl-1-benzyl-1,2,3-triazole (1.8 g.), m.p. 171°-173° C., suitable for use in the next stage of the preparation. An aliquot was recrystallised from ethanol to give pure 5-benzamido-4-benzoylcarbamoyl-1-benzyl-1,2,3-triazole, m.p. 182°-186° C.

Workup

  1. temperaturecooled
  2. customprepared
  3. stirringStirring
  4. customThe clear solution which formed
  5. filtrationthe precipitated solid was filtered off
  6. washwashed well with water and diethyl ether

Sources & evidence

ORD record
ord-6d89605fd3f844968b82e5b2d0d21377
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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