Sodium Hydroxide → HCID 67553246, compound

A mixture of 5-aminotetrazole (6.0 g, 58.2 mmol) and solid sodium hydroxide (8.36 g, 208 mmol) in acetonitrile (30 ml) was stirred for 0.5h. 2-Chloroethylamine hydrochloride (7.26 g, 62.4 mmol) and tetrabutylammonium hydrogen sulphate (0.788 g 2.32 mmol) were added and the reaction was heated at reflux for 18h. The mixture was filtered and the filtrate was evaporated to leave an oil which was taken up in 48% aqueous HBr. The solution was diluted with ethanol (150 ml) and then evaporated to leave an oil which soon solidified. The solid was leached with hot ethanol leaving a brown gum which was dissolved in water and the solution was evaporated to dryness to give a solid (1.62 g) after drying. The ethanol was reduced in volume and allowed to crystallise. The resulting solid (0.879 g) and the solid from the aqueous solution were combined and stirred in ethanol with a slight excess of sodium hydroxide until a clear solution was obtained. This solution was preabsorbed onto flash silica and purified by elution with dichloromethane:ethanol:0.88 ammonia (100:8:1) to (30:8:1). Fractions with product were evaporated to leave the title compound (0.217 g) as an oil. MH+ =129.

1. temperaturethe reaction was heated
2. temperatureat reflux for 18h
3. filtrationThe mixture was filtered
4. customthe filtrate was evaporated
5. customto leave an oil which
6. customevaporated
7. customto leave an oil which
8. customthe solution was evaporated to dryness

ORD record

ord-69339d99b0764f088bb45e8fbf87d5dc

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05925624