Dichloromethane → 2-(2-Chlorophenyl)-5-(methylamino)-4-(4-methylpyridin-2-yl)furan-3(2H)-one

HRID 1419856ノート

反応式

HRID 1419856 の反応式
[OH-].[Na+].[CH2:3](Cl)Cl.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:17](=[O:18])[C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)=[C:15]([NH2:26])[O:14]1.S(OC)(OC)(=O)=O>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]1[C:17](=[O:18])[C:16]([C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)=[C:15]([NH:26][CH3:3])[O:14]1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 70197198HCID 70197198、化合物

生成物 1

HCID 451199902-(2-Chlorophenyl)-5-(methylamino)-4-(4-methylpyridin-2-yl)furan-3(2H)-one収率 88%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 962Water溶媒

実験手順

Solid sodium hydroxide(180 mg, 4.50 mmol) was dissolved in a small amount of water and then added to methylene chloride (8.6 ml) containing 2-(o-chlorophenyl)-3-oxo-4-(4-methylpyridyl)-5-amino-2,3-dihydrofuran(400 mg, 1.3 mmol). Tetrabutylammonium bromide (50.0 mg, 1.37 mmol) was added and then a mixture containing dimethyl sulfate (164 mg, 1.30 mmol) was slowly added at room temperature. The mixture was stirred at room temperature for one hour and then washed twice with water, dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo to yield a crude product, which was separated by column-chromatography over silica gel to obtain the desired product (370 mg, yield=88%) as a white solid.

後処理

  1. additionwas slowly added at room temperature
  2. washwashed twice with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customto yield a crude product, which
  6. customwas separated by column-chromatography over silica gel

出典と根拠

ORDレコード
ord-5d716ce897b04124bd79547a7d4d0f6f
出典データセット
uspto-grants-1999_03
特許番号
US05889027

反応ノート

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