Reaktion #66959

Reaktionsgleichung

diphenyldithiophosphonic acid

2-cyano-2-methylpropionic acid ethyl ester

→

title compound

Ausbeute 22.2%

ethyl 3-amino-2,2-dimethyl-3-thioxopropanoate

Ausbeute 22.2%

Lösungsmittel

isopropanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 4 h
3. 3
   SonstigeReaction mixture
4. 4
   Sonstigea precipitate was formed
5. 5
   SonstigeReaction flask
6. 6
   SonstigeReaction mixture
7. 7
   Filtrationwas filtered
8. 8
   Einengenfiltrate was concentrated
9. 9
   Waschenwashed with water (20 mL), 1N NaOH (20 mL), saturated NaHCO3 (20 mL)
10. 10
    Trocknendried over sodium sulfate
11. 11
    Einengenconcentrated
12. 12
    Wascheneluted with linear gradient 0-50% hexane-ethyl acetate

Vorschrift

A mixture of diphenyldithiophosphonic acid (ALFAAESAR, 1.42 g, 5.67 mmol) and 2-cyano-2-methylpropionic acid ethyl ester (ABCR, 0.412 mL, 2.83 mmol) in isopropanol (30 mL) was heated under reflux for 4 h. Reaction mixture was cooled to room temperature and a precipitate was formed. Reaction flask was placed in the freezer for 1 h. Reaction mixture was filtered and filtrate was concentrated. Residue was taken up in DCM (100 mL) and washed with water (20 mL), 1N NaOH (20 mL), saturated NaHCO3 (20 mL) and dried over sodium sulfate and concentrated. The resulting oil was loaded on a 25 g silica cartridge and eluted with linear gradient 0-50% hexane-ethyl acetate to yield the title compound (110 mg, 0.628 mmol, 22.2% yield). Another impure batch was loaded on a 10 g silica cartridge and eluted with linear gradient 0-50% hexane-ethyl acetate to recover the title compound (120 mg, 0.685 mmol, 24.17% yield). Total yield: (230 mg, 1.313 mmol, 46.32%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.70 (br s, 1H), 8.86 (br s, 1H), 4.05 (q, 2H), 1.39 (s, 6H), 1.15 (t, 3H). [ES+MS] m/z 176 (MH+).

Quelle