Hydrochloric Acid → S-Biphenyl-3-yl O-ethyl carbonodithioate

To a solution of 1 equiv. of biphenyl-3-amine (1 g, 5.92 mmol) in water (7.3 mL) at 0° C. was added concentrated hydrochloric acid (1 mL). A cold solution of 1.1 equiv. of sodium nitrite (450 mg, 6.5 mmol) in water (3 mL) was added slowly and stirred for 15 min. The cold diazonium solution was added slowly to a solution of 1.3 equiv. of potassium ethyl xanthate (1.16 g, 1.3 mmol) in water (1.3 mL) at 45° C. The reaction mixture was stirred for an additional 30 min at 45° C. and then cooled to RT. The reaction mixture was extracted with diethyl ether (3×50 mL). The combined organic extracts were washed with 1 N NaOH solution (100 mL), water (3×50 mL), brine (50 mL), dried over MgSO4, filtered and evaporated under reduced pressure. The resulting crude xanthate 52a was used directly in the next step without further purification. MS (ESI) m/z 275.0 (M+H)+.

1. stirringThe reaction mixture was stirred for an additional 30 min at 45° C.
2. extractionThe reaction mixture was extracted with diethyl ether (3×50 mL)
3. washThe combined organic extracts were washed with 1 N NaOH solution (100 mL), water (3×50 mL), brine (50 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe resulting crude xanthate 52a was used directly in the next step without further purification

ORD-Eintrag

ord-dd8fc80eba9440f9959b5863aaa8d58b

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08822513B2