Triethylamine → 1-Dipropylcarbamoyl-3-propylsulphonyl-1,2,4-triazole

Dipropylcarbamoyl chloride (5.4 g.) was added to a solution of 5.25 g. 3-propylsulphonyl-1,2,4-triazole and 6 ml. dry triethylamine in 25 ml. dry tetrahydrofuran and the resulting mixture was refluxed under anhydrous conditions for 2.5 hours. The cooled reaction mixture was filtered to remove triethylamine hydrochloride, the filtrate was distilled under reduced pressure to remove solvent, and the residue was dissolved in methylene dichloride. The resulting solution was washed with ice-cold 0.1N aqueous sodium hydroxide (2 × 50 ml.), then with 0.01N aqueous sulphuric acid (50 ml.) and finally with water. The resulting solution was dried over anhydrous sodium sulphate and was then distilled under reduced pressure to give a solid residue. This residue was recrystallized twice from petroleum ether (b.p. 60° - 80° C.) to give 1-dipropylcarbamoyl-3-propylsulphonyl-1,2,4-triazole, m.p. 79° - 80° C. Elemental analysis satisfactory.

1. customThe cooled reaction mixture
2. filtrationwas filtered
3. customto remove triethylamine hydrochloride
4. distillationthe filtrate was distilled under reduced pressure
5. customto remove solvent
6. dissolutionthe residue was dissolved in methylene dichloride
7. washThe resulting solution was washed with ice-cold 0.1N aqueous sodium hydroxide (2 × 50 ml.)
8. dry with materialThe resulting solution was dried over anhydrous sodium sulphate
9. distillationwas then distilled under reduced pressure
10. customto give a solid residue
11. customThis residue was recrystallized twice from petroleum ether (b.p. 60° - 80° C.)

ORD record

ord-8ce8a0432b9a4e689c0b057977917636

Source dataset

uspto-grants-1978_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04087269