Water → HCID 178422622, compound

HRID 653575Notes

Reaction equation

HRID 653575 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([SH:7])[NH:4][N:3]=1.[C:8]([CH2:16][C:17](=O)[CH3:18])(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)Cl.O>C(O)(=O)C>[CH3:18][C:17]1[CH:16]=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]2[N:4]=[C:5]([SH:7])[N:6]=[C:2]2[N:1]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 7166BenzoylacetoneHCID 1785092965-amino-1H-1,2,4-triazole-3-thiol

Product 1

HCID 178422622HCID 178422622, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 10.0 9 (86 mmol) 3-amino-5-mercapto-1,2,4-triazole and 14.0 g (86.5 mmol) of benzoylacetone in 100 ml of glacial acetic acid was heated at reflux 4 hours. Methylene chloride (500 ml) and excess water were added. The organic layer was separated and washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give a residue to which n-butyl chloride was added. Filtering gave 4.9 g of crude 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-thiol which was used directly in the next step.

Workup

  1. temperaturewas heated
  2. temperatureat reflux 4 hours
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give a residue to which n-butyl chloride
  8. additionwas added
  9. filtrationFiltering

Sources & evidence

ORD record
ord-6562ce2a6b7a44e1826e6920a4812465
Source dataset
uspto-grants-1992_07
Patent number
US05127936

Reaction notes

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