Ethyl 2-cyanopropionate → Ethyl 2-carbamothioyl-2-methylacetate

HRID 38677

Reaction equation

HRID 38677 reaction equation
C1(P(C2C=CC=CC=2)(S)=[S:8])C=CC=CC=1.[CH2:16]([O:18][C:19](=[O:24])[CH:20]([C:22]#[N:23])[CH3:21])[CH3:17]>C(O)(C)C>[NH2:23][C:22](=[S:8])[CH:20]([CH3:21])[C:19]([O:18][CH2:16][CH3:17])=[O:24]

Participants

4

Reactant 2

HCID 98018Ethyl 2-cyanopropionateHCID 129564P,P-Diphenylphosphinodithioic acid

Product 1

HCID 11819343Ethyl 2-carbamothioyl-2-methylacetate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of diphenylphosphinodithioic acid (Alfa-Aesar) (7.48 g, 29.9 mmol) and 2-cyanopropionic acid ethyl ester (ABCR, 1.980 mL, 14.94 mmol) in isopropanol (80 mL) was heated under reflux for 8 h then stood at rt overnight. Reaction mixture was filtered and filtrate was diluted with EtOAc and washed with 1N NaOH, brine, and dried over Na2SO4. Crude was purified by chromatography on silica gel using a Hex/EtOAc gradient. Appropriate fractions were combined and evaporated to yield title compound as a yellow oily solid. 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+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 8 h
  3. customReaction mixture
  4. filtrationwas filtered
  5. additionfiltrate was diluted with EtOAc
  6. washwashed with 1N NaOH, brine
  7. dry with materialdried over Na2SO4
  8. customCrude was purified by chromatography on silica gel using a Hex/EtOAc gradient
  9. customevaporated

Sources & evidence

ORD record
ord-a4269f398c3c4f09ab7956624613465b
Source dataset
uspto-grants-2013_09
Patent number
US08524750B2

Linked notes

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