Hydrochloric Acid → 2-[5-(Benzylsulfanyl)-1H-tetrazol-1-yl]ethan-1-ol

A mixture of 4-(2-hydroxyethyl)thiosemicarbazide (10.3 g), benzyl chloride (10.6 g), water (30 ml) and methanol (60 ml) was stirred for 20 hours at room temperature to give a homogeneous solution containing benzyl N-(2-hydroxyethyl)thiocarbazimidate. The solution was ice-cooled and thereto was little by little added sodium nitrite (5.24 g) with stirring and then dropwise added conc. hydrochloric acid (3.5 ml) over a period of 30 mimetes. The resulting mixture was stirred for an hour under ice-cooling. To the reaction mixture were added potassium carbonate (18 g) and water (30 ml). The mixture was stirred and then concentrated under reduced pressure. The concentrate was extracted with chloroform and the extract was washed with water, dried over magnesium sulfate and then evaporated under reduced pressure. The residual oil was subjected to column chromatography on silica gel. The fractions containing the object compound were collected to give an oil of 1-(2-hydroxyethyl)-5-benzylthio-1H-tetrazole (12.1 g).

1. customto give a homogeneous solution
2. temperaturecooled
3. stirringwith stirring
4. stirringThe resulting mixture was stirred for an hour under ice-
5. temperaturecooling
6. stirringThe mixture was stirred
7. concentrationconcentrated under reduced pressure
8. extractionThe concentrate was extracted with chloroform
9. washthe extract was washed with water
10. dry with materialdried over magnesium sulfate
11. customevaporated under reduced pressure
12. additionThe fractions containing the object compound
13. customwere collected

ORD record

ord-f3bfbe777e8c4ccbb086a8c94e6fb708

Source dataset

uspto-grants-1986_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04563524