Water → 1-(4-Chloro-benzoyl)-3-methylthio-5-amino-1,2,4-triazole

HRID 485690Notes

Reaction equation

HRID 485690 reaction equation
N1C=CC=CC=1.[CH3:7][S:8][C:9]1[N:13]=[C:12]([NH2:14])[NH:11][N:10]=1.[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1.O>O1CCOCC1>[Cl:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:11]2[C:12]([NH2:14])=[N:13][C:9]([S:8][CH3:7])=[N:10]2)=[O:21])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 784713-(Methylthio)-1,2,4-triazol-5-amine

Product 1

HCID 135736171-(4-Chloro-benzoyl)-3-methylthio-5-amino-1,2,4-triazoleYield 83.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
-5 °C

Procedure

4.7 g of pyridine are added to a solution of 7.8 g of 3-methylthio-5-amino-1H-1,2,4-triazole [Monatshefte fur Chemie 106, 1291 (1975)] in 200 ml of dioxane, then 10.8 g of 4-chloro-benzoylchloride are added dropwise at -5° C. The reaction mixture is stirred for one hour at -5° C., then for a further one hour at room temperature, finally 100 ml of water are added at water-cooling and the entire mixture is extracted with chloroform. The chloroform layer is washed with water, dried, evaporated to dryness, yielding 13.46 g (83.5 percent) of 1-(4-chloro-benzoyl)-3-methylthio-5-amino-1,2,4-triazole, m.p. 175° to 177° C. (following boiling with alcohol).

Workup

  1. waitfor a further one hour at room temperature
  2. temperaturecooling
  3. extractionthe entire mixture is extracted with chloroform
  4. washThe chloroform layer is washed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-cab4ae92e214483fa5e34e0c5f2c7c0d
Source dataset
uspto-grants-1985_08
Patent number
US04537899

Reaction notes

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