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

HRID 38677

반응식

HRID 38677 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]>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

4

반응물 2

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

생성물 1

HCID 11819343Ethyl 2-carbamothioyl-2-methylacetate

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-a4269f398c3c4f09ab7956624613465b
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524750B2

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