Ethyl Acetate → Ethyl 2-carbamothioyl-2-methylacetate

HRID 1625081노트

반응식

HRID 1625081 반응식
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].CCOC(C)=O>C(O)(C)C>[NH2:23][C:22](=[S:8])[CH:20]([CH3:21])[C:19]([O:18][CH2:16][CH3:17])=[O:24]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 98018Ethyl 2-cyanopropionateHCID 129564P,P-Diphenylphosphinodithioic acid

생성물 1

HCID 11819343Ethyl 2-carbamothioyl-2-methylacetate수율 54.8%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-5d273aabe5ad4cf19e3c30d4d91b1db4
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779153B2

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