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Sodium hydride → 2-(2-Cyanovinyl)-4,5-dimethoxyphenyl dimethylsulphamate

HRID 420865
ノート
印刷プレビュー

反応式

HRID 420865 の反応式
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH3:14][N:15]([CH3:32])[S:16](=[O:31])(=[O:30])[O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:19]=1[CH:28]=O.C(=O)([O-])O.[Na+]>C1COCC1.O>[CH3:14][N:15]([CH3:32])[S:16](=[O:31])(=[O:30])[O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[CH:20][C:19]=1[CH:28]=[CH:5][C:3]#[N:4]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 516892Sodium BicarbonateHCID 866430082-Formyl-4,5-dimethoxyphenyl dimethylsulphamate

生成物 1

HCID 666575792-(2-Cyanovinyl)-4,5-dimethoxyphenyl dimethylsulphamate収率 80%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-10 °C

実験手順

Add 3.1 g (0.0773 mol) of sodium hydride in portions to a solution at 0° C. of 11.9 ml (0.0736 mol) of diethyl cyanomethylphosphonate in 400 ml of THF. Cool the mixture to −10° C. and add dropwise a suspension of 21.3 g (0.0736 mol) of 2-formyl-4,5-dimethoxyphenyl dimethylsulphamate in 200 ml of THF. Stir for 30 minutes and hydrolyse with 600 ml of a solution of sodium hydrogen carbonate and water (50/50) and then extract the solution twice with 300 ml of toluene each time. The organic phase is washed with 100 ml of water and 100 ml of saturated aqueous NaCl solution and then dried over MgSO4, filtered and evaporated to dryness. The residue obtained is crystallised in 80 ml of diisopropyl ether at ambient temperature and then filtered and washed with 20 ml of diisopropyl ether and dried in vacuo. 18.4 g of title product are obtained.

後処理

  1. additionadd dropwise
  2. extractionextract the solution twice with 300 ml of toluene each time
  3. washThe organic phase is washed with 100 ml of water and 100 ml of saturated aqueous NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue obtained
  8. customis crystallised in 80 ml of diisopropyl ether at ambient temperature
  9. filtrationfiltered
  10. washwashed with 20 ml of diisopropyl ether
  11. customdried in vacuo

出典と根拠

ORDレコード
ord-6a88d8d1b84d4a58ac0174966fbe5fa7
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097720B2

反応ノート

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