Benzoyl chloride → 5-Benzamido-3-mercapto-1,2,4-triazole

HRID 275033Notes

Reaction equation

HRID 275033 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([SH:7])[N:3]=1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:8]([NH:1][C:2]1[NH:6][N:5]=[C:4]([SH:7])[N:3]=1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 178509066HCID 178509066, compound

Product 1

HCID 1785226075-Benzamido-3-mercapto-1,2,4-triazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suitably equipped reaction vessel was charged 116 g (1.0 mole) of 5-amino-3-mercapto-1,2,4-triazole and 500 ml of pyridine. A total of 147.5 g (1.05 mole) of benzoyl chloride was added with vigorous stirring over 25 minutes, during which time the temperature rose from 24° to 59° C. The mobile, pale yellow slurry obtained was heated at reflux with stirring. The solid material dissolved and then, after about 40 additional minutes, a white solid began separating. An additional 200 ml of pyridine was added to aid mixing and the reaction was continued at 117°-122° for a total of 7 hours. The thick, white slurry obtained was filtered, washed with water and with methylene chloride, and dried to obtain 186 g (84 percent of theory) of the title compound, m.p. 311°-312° (dec.).

Workup

  1. customTo a suitably equipped reaction vessel
  2. customrose from 24° to 59° C
  3. customThe mobile, pale yellow slurry obtained
  4. temperaturewas heated
  5. temperatureat reflux
  6. stirringwith stirring
  7. dissolutionThe solid material dissolved
  8. customafter about 40 additional minutes, a white solid began separating
  9. additionAn additional 200 ml of pyridine was added to aid
  10. additionmixing
  11. customwas continued at 117°-122° for a total of 7 hours
  12. customThe thick, white slurry obtained
  13. filtrationwas filtered
  14. washwashed with water and with methylene chloride
  15. customdried

Sources & evidence

ORD record
ord-e494719280c444fd9874f8bc3711db46
Source dataset
uspto-grants-1995_02
Patent number
US05391759

Reaction notes

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