Hydrochloric Acid → HCID 53668406, compound

A 50% w/w dispersion of sodium hydride in oil (0.5 g.) was added in portions to propane-1,3-diol (5 ml.) and the mixture stirred at room temperature for 1 hour. 2-Amino-6-bromopyridine (0.85 g.) was added and the mixture stirred at 150° for 4 hours and then cooled to room temperature. The mixture was taken up in N aqueous HCl and washed with EtOAc and the aqueous phase basified with 10 N aqueous NaOH. The mixture was extracted three times with EtOAc and the combined extracts dried and evaporated to dryness to give a brown oil (1.6 g.). A portion of the oil (0.67 g.) was dissolved in acetonitrile (5 ml.) and the solution treated with 2,2,2-trifluoroethylisothiocyanate (0.3 g.). The mixture was kept at room temperature for 18 hours and then evaporated to dryness and the residue recrystallised from EtOH to give 6-[3-(2,2,2-trifluoroethyl)thioureido]-2-(3-hydroxypropoxy)pyridine (0.18 g.), m.p. 123°-124°.

1. stirringthe mixture stirred at 150° for 4 hours
2. temperaturecooled to room temperature
3. washwashed with EtOAc
4. extractionThe mixture was extracted three times with EtOAc
5. customthe combined extracts dried
6. customevaporated to dryness
7. customto give a brown oil (1.6 g.)
8. waitThe mixture was kept at room temperature for 18 hours
9. customevaporated to dryness
10. customthe residue recrystallised from EtOH

ORD record

ord-bd0fc0bfdeca4499bcecc4eecba5ec17

Source dataset

uspto-grants-1984_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04451463