Hydrochloric Acid → HCID 19600315, compound

Temperature

0 °C

A 1.04 g sample of 3-chloro-4-butylthio-1,2,5-thiadiazole was dissolved in 20 mL of THF and added to a 50 mL reaction vessel. The mixture was cooled to 0° C. A 10 mL sample of sodium bis(trimethylsilyl)amide in THF (1.0M) was added dropwise to the reaction vessel. The mixture was stirred at 0° C. The reaction was quenched using 50 mL water upon desired completion of reaction. The pH of the mixture was adjusted to 2.0 using HCl. The mixture was stirred for 15 min. and then adjusted to pH=11 using NaOH. The mixture was extracted using ether. The organic layers were combined, dried, and filtered. The filtrate was concentrated to dryness. The resulting product was purified using column chromatography. Yield: 1.07 g (65%). The N,N-bis(trimethylsilyl)-3-amino-4-butylthio-1,2,5-thiadiazole was suspended in 3N HCl and heated to about 50° C. The mixture was stirred for 3 h. The pH was adjusted to 11 using NaOH. The mixture was extracted using t-butylmethyl ester. The organics were combined, dried, filtered and concentrated to dryness. Yield: 0.43 g (45%). (Compound 66). The process substantially as described was repeated to yield 82% of the desired 3-amino-4-butylthio-1,2,5-thiadiazole.

1. additionadded to a 50 mL reaction vessel
2. customThe reaction was quenched
3. customcompletion of reaction
4. stirringThe mixture was stirred for 15 min.
5. extractionThe mixture was extracted
6. customdried
7. filtrationfiltered
8. concentrationThe filtrate was concentrated to dryness
9. customThe resulting product was purified
10. temperatureheated to about 50° C
11. stirringThe mixture was stirred for 3 h
12. extractionThe mixture was extracted
13. customdried
14. filtrationfiltered
15. concentrationconcentrated to dryness

ORD record

ord-bc59f3c805ba4d69956f18a014844a53

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05646289