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

HRID 1419856노트

반응식

HRID 1419856 반응식
[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

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 70197198HCID 70197198, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5d716ce897b04124bd79547a7d4d0f6f
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05889027

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