Réaction #95981

Équation de réaction

thiosemicarbazide

ethyl alcohol

sodium nitrite

benzyl chloride

→

5-Benzylthio-1H-tetrazole

Solvants

ethyl acetate

water

Conditions de réaction

Traitement

1. 1
   TempératureAfter heating
2. 2
   Autrethe reaction mixture was evaporated to dryness under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in water
4. 4
   LavageThe solution was washed with ethyl acetate
5. 5
   workup.ADDITIONwas added to a solution of 25 g
6. 6
   AutreThe organic layer was separated
7. 7
   Lavagewashed with water, brine
8. 8
   Séchagewas dried over sodium sulfate
9. 9
   AutreThe dried ethyl acetate solution was evaporated under reduced pressure
10. 10
    Autrethe product obtained as a residue
11. 11
    Lavagewas washed with methylene chloride
12. 12
    Autrerecrystallized from ethyl acetate
13. 13
    AutreThere were obtained 21 g

Mode opératoire

A solution of 30 g. (0.33 mole) of thiosemicarbazide and 51 g. (0.40 mole) of benzyl chloride in 500 ml. of ethyl alcohol was heated at the reflux temperature for about 3.5 hours. After heating, the reaction mixture was evaporated to dryness under reduced pressure and the residue was dissolved in water. The solution was washed with ethyl acetate and was added to a solution of 25 g. (0.36 mole) of sodium nitrite in 50 ml. of water. The solution was stirred for 15 minutes and then ethyl acetate was added. The organic layer was separated and washed with water, brine, and was dried over sodium sulfate. The dried ethyl acetate solution was evaporated under reduced pressure, and the product obtained as a residue was washed with methylene chloride and recrystallized from ethyl acetate. There were obtained 21 g. of the product melting at about 134° C. to about 136° C.

Source