Ethyl Acetate → Ethyl 2-carbamothioyl-2-methylacetate

A mixture of diphenylphosphinodithioic acid (ALFAAESAR, 37.4 g, 149 mmol) and 2-cyanopropionic acid ethyl ester (ABCR, 9.90 mL, 74.7 mmol) in isopropanol (350 mL) was heated under reflux for 5 h. TLC (Hex:EtOAc 7:3) showed reaction had gone to completion. Reaction mixture was allowed to cool and was placed in the fridge overnight. Reaction mixture was filtered off and washed with isopropanol. Residue was partitioned between ethyl acetate (250 mL) and 1N NaOH (250 mL). Phases were separated and organic phase was washed with water (300 mL), brine (300 mL), dried over sodium sulfate and concentrated to dryness. Crude was purified by chromatography on silica gel using a hexane/EtOAc gradient. Appropriate fractions were combined and evaporated to yield title compound as a white solid (6.6 g, 40.9 mmol, 54.8% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 9.60 (s, 1H), 9.40 (s, 1H), 4.05 (q, 2H), 3.74 (q, 1H), 1.29 (d, 3H), 1.15 (t, 3H). [ES+MS] m/z 162 (MH+).

1. temperaturewas heated
2. temperatureunder reflux for 5 h
3. customreaction
4. customReaction mixture
5. temperatureto cool
6. customwas placed in the fridge overnight
7. customReaction mixture
8. filtrationwas filtered off
9. washwashed with isopropanol
10. customResidue was partitioned between ethyl acetate (250 mL) and 1N NaOH (250 mL)
11. customPhases were separated
12. washorganic phase was washed with water (300 mL), brine (300 mL)
13. dry with materialdried over sodium sulfate
14. concentrationconcentrated to dryness
15. customCrude was purified by chromatography on silica gel using a hexane/EtOAc gradient
16. customevaporated

ORD-Eintrag

ord-b08789d4b8364c468562b26294cbcc5b

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09000181B2