Thioglycolic Acid → HCID 21190753, compound

To 11 g (50 mmol) of 2-,2′-dipyridyl disulfide and 8.4 mL (60 mmol) of triethyl amine in 100 mL of tetrahydrofuran at 0° C. as added 2.8 mL (40 mmol) of mercaptoacetic acid in 5 mL of tetrahydrofuran. The ice bath was removed and after one hour 6.8 mL (65 mmol) tert-butyl thiol was added. The reaction was allowed to stir overnight at ambient temperature before diluting with ether and washing three times with 1N aqueous HCl. The product was then extracted into 10% aqueous NaOH. The aqueous phase was washed twice with ether and then acidified with HCl to pH ˜3.5. The product was extracted with ether, dried with Na2SO4, filtered and evaporated under reduced pressure to give a crude product. This material was distilled by Kugelrohr distillation to give 6.6 g (37 mmol, 92%) of partially purified product. This material was used in the next step without further purification.

1. additionwas added
2. washwashing three times with 1N aqueous HCl
3. extractionThe product was then extracted into 10% aqueous NaOH
4. washThe aqueous phase was washed twice with ether
5. extractionThe product was extracted with ether
6. dry with materialdried with Na2SO4
7. filtrationfiltered
8. customevaporated under reduced pressure

ORD record

ord-edeb0150408b40e5bcff9b34d3db146c

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06251912B1