Hydrochloric Acid → HCID 86737880, compound

Temperature

-30 °C

Dry hydrogen chloride is bubbled through a suspension of penicillamine (25 g, 0.167 mole) in 300 ml of dry ethanol until all is in solution. The warm solution is then cooled in an ice bath to 0°-5° C. and saturated with dry HCl. The ice bath is removed and the reaction mixture is heated to reflux for 2 hours, then is concentrated in vacuo to a viscous golden oil which is cooled (-30° C.) overnight. After warming to room temperature, the material, now a mixture of white crystalline solid and oil, is triturated with 500 ml Et2O for 30 minutes, then is filtered. An insoluble oil passes through the filter funnel with the Et2O and the residue is washed (3 times, 150 ml portions) further with Et2O. After drying on the funnel under a stream of dry N2, 14.14 g (mp 125°-145° C., 39% yield) of the desired product is obtained as white powder. NMR (CDCl3 ) δ8.85 (bs, 3, --NH3Cl), 4.34 (q, 2, J=7 Hz, OCH2 --C), 4.6-4.15 (m, 1, NCHCO2); 3.83 (s, 1, --SH), 1.70 (s, 3, C--CH3), 1.59 (s, 3, C--CH3), 1.35 (t, 3, J=7 Hz, OCH2CH3); IR (KBr): 1725 cm-1 (s) (C=O).

1. customThe ice bath is removed
2. temperaturethe reaction mixture is heated
3. temperatureto reflux for 2 hours
4. concentrationis concentrated in vacuo to a viscous golden oil which
5. temperatureAfter warming to room temperature
6. additionthe material, now a mixture of white crystalline solid and oil
7. customis triturated with 500 ml Et2O for 30 minutes
8. filtrationis filtered
9. washAn insoluble oil passes through the filter funnel with the Et2O and the residue is washed (3 times, 150 ml portions) further with Et2O
10. dry with materialAfter drying on the funnel under a stream of dry N2

ORD record

ord-6185a3159f314a31a66b9420c68dfb6e

Source dataset

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04279900