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

HRID 38677

反応式

HRID 38677 の反応式
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]

参加物

4

反応物 2

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

生成物 1

HCID 11819343Ethyl 2-carbamothioyl-2-methylacetate

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-a4269f398c3c4f09ab7956624613465b
出典データセット
uspto-grants-2013_09
特許番号
US08524750B2

関連ノート

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