Hydrochloric Acid → HCID 21504430, compound

HRID 1288293Notes

Reaction equation

HRID 1288293 reaction equation
[CH2:1]([N:8]1[C:12]([NH:13][CH:14]=[O:15])=[C:11]([C:16](=[O:18])[NH2:17])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.Cl>[OH-].[Na+]>[C:14]([NH:13][C:12]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=[N:10][C:11]=1[C:16](=[O:18])[NH2:17])(=[O:15])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7412Benzoyl chlorideHCID 21504481HCID 21504481, compound

Product 1

HCID 21504430HCID 21504430, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
0 °C

Procedure

1-Benzyl-4-carbamoyl-5-formamido-1,2,3-triazole (40 g.; prepared as described by A. Albert, J.Chem.Soc., 1969 (C), 152) was dissolved in 2N sodium hydroxide solution (156 ml.), and treated with alternate successive portions of benzoyl chloride (total 24 ml.) and 2N aqueous sodium hydroxide solution (total 140 ml.) with vigorous agitation, and cooling with ice, over a period of 2 hours. The solution was then acidified to pH 4 with concentrated hydrochloric acid, again cooling with ice, and the precipitated solid was filtered off, dissolved in 2N sodium hydroxide solution (208 ml.) and the solution stirred at 0° C. while portions of benzoyl chloride (total 57 ml.) and 2N sodium hydroxide solution (total 331 ml.) were added alternately over 45 minutes. The resultant mixture was stirred for a further 60 minutes at 0° C. before being acidified to pH 4 with concentrated hydrochloric acid, the temperature being maintained at 0° C. The solid was filtered off and washed successively with water, diethyl ether and water. The solid product was dried, and recrystallised from ethanol to give 5-benzamido-1-benzyl-4-carbamoyl-1,2,3-triazole (23.1 g.), m.p. 191°-192° C.

Workup

  1. customprepared
  2. temperaturecooling with ice, over a period of 2 hours
  3. temperatureagain cooling with ice
  4. filtrationthe precipitated solid was filtered off
  5. dissolutiondissolved in 2N sodium hydroxide solution (208 ml.)
  6. additionwere added alternately over 45 minutes
  7. stirringThe resultant mixture was stirred for a further 60 minutes at 0° C.
  8. temperaturethe temperature being maintained at 0° C
  9. filtrationThe solid was filtered off
  10. washwashed successively with water, diethyl ether and water
  11. customThe solid product was dried
  12. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-6889c89bc86345e6ba01f8439fd12d29
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

Loading…