Ethanol → Benzylsulfanylmethyl-5-cyclopropyl-imidazolidine-2,4-dione

HRID 1441502ノート

反応式

HRID 1441502 の反応式
[CH2:1]([S:8][CH2:9]C(C1CC1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23].[CH3:24][C:25](OC)([CH3:27])C.[CH2:30]([OH:32])[CH3:31]>O>[CH3:5][CH2:4][CH2:3][CH:2]([CH3:7])[CH3:1].[CH2:1]([S:8][CH2:9][N:22]1[CH:31]([CH:27]2[CH2:24][CH2:25]2)[C:30](=[O:32])[NH:23][C:18]1=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 5

HCID 702EthanolHCID 8929Sodium CyanideHCID 15413tert-Butyl methyl etherHCID 517111Ammonium CarbonateHCID 639056732-(Benzylsulfanyl)-1-cyclopropylethan-1-one

生成物 2

HCID 78922-MethylpentaneHCID 66734956Benzylsulfanylmethyl-5-cyclopropyl-imidazolidine-2,4-dione収率 32.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

2-Benzylsulfanyl-1-cyclopropyl-ethanone (27.55 g, 0.133 mol) was dissolved in ethanol (250 ml) and dispensed into 20×40 ml vials. Sodium cyanide (6.52 g, 0.133 mol) and ammonium carbonate (64 g, 0.667 mol) were dissolved in water (250 ml) and divided into the vials, which were then sealed and heated at 90° C. for 5 h behind a safety screen. After cooling to room temperature, the contents of the vials were combined, TBME was added, and the mixture was washed with water (×2), brine (×1), and then dried over sodium sulphate. Evaporation then gave the crude product (16.5 g, 45%). This material was absorbed onto silica and chromatographed (5×9.5 cm column of silica) eluting with iso-hexane to 50% ethyl acetate:iso-hexane to yield the title compound (11.81 g, 32.1%).

後処理

  1. customwere then sealed
  2. temperatureAfter cooling to room temperature
  3. washthe mixture was washed with water (×2), brine (×1)
  4. dry with materialdried over sodium sulphate
  5. customEvaporation
  6. customthen gave the crude product (16.5 g, 45%)
  7. customThis material was absorbed onto silica
  8. customchromatographed (5×9.5 cm column of silica)
  9. washeluting with iso-hexane to 50% ethyl acetate

出典と根拠

ORDレコード
ord-645ad512b6504166b683bdff146d5ff8
出典データセット
uspto-grants-2010_02
特許番号
US07655664B2

反応ノート

読み込み中…