Benzoyl chloride → HCID 178513861, compound

HRID 1288304Notes

Reaction equation

HRID 1288304 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[NH:15][N:14]=[N:13][C:12]=1[C:16](=[O:18])[NH2:17]>[OH-].[Na+]>[C:1]([NH:10][C:11]1[NH:15][N:14]=[N:13][C:12]=1[C:16](=[O:18])[NH2:17])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178513860HCID 178513860, compound

Product 1

HCID 178513861HCID 178513861, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

Benzoyl chloride (3.26 ml.) and 4N aqueous sodium hydroxide solution (8 ml.) were added alternately, in portions over 25 minutes, to a vigorously shaken, ice-cooled solution of 5-amino-4-carbamoyl-1H-1,2,3-triazole (1.27 g; prepared by the method of J. R. E. Hoover and A. R. Day, J. Amer. Chem. Soc., 1956, 78,5832) in 4N aqueous sodium hydroxide solution (15 ml.). The reaction mixture was extracted with diethyl ether, the aqueous layer cooled and acidified with concentrated hydrochloric acid, and the white precipitate filtered off and washed well with water. The crude solid was stirred in diethyl ether and then purified by dissolving in dilute aqueous sodium hydroxide solution, and reprecipitation by the addition of concentrated hydrochloric acid. The solid was filtered off, washed with water, and dried to give 5-benzamido-4-carbamoyl-1H-1,2,3-triazole (0.085 g.), m.p. 299° C. (with decomposition).

Workup

  1. customprepared by the method of J
  2. extractionThe reaction mixture was extracted with diethyl ether
  3. temperaturethe aqueous layer cooled
  4. filtrationthe white precipitate filtered off
  5. washwashed well with water
  6. stirringThe crude solid was stirred in diethyl ether
  7. custompurified
  8. dissolutionby dissolving in dilute aqueous sodium hydroxide solution
  9. customreprecipitation
  10. additionby the addition of concentrated hydrochloric acid
  11. filtrationThe solid was filtered off
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-8e2f3ac778124b22a7db25f6e04cd72d
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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