Dimethyl Sulfate → 3-(4-Choro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1h, 3h)-pyrimidinedione

HRID 277430ノート

反応式

HRID 277430 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[NH:10][C:9]2=[O:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.S(OC)(O[CH3:27])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:17])([F:18])[F:16])[N:10]([CH3:27])[C:9]2=[O:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1

参加物

5

反応物 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 570852913-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4 (1H, 3H)-pyrimidinedione

生成物 1

HCID 569765863-(4-Choro-2-nitrophenyl)-1-methyl-6-trifluoromethyl-2,4(1h, 3h)-pyrimidinedione収率 73.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
55 °C

実験手順

A mixture of 3-(4-chloro-2-nitrophenyl)-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (3 g), dimethyl sulfate (1.7 g) and potassium carbonate (1.85 g) in N,N-dimethylformamide (100 ml) was stirred at 55° C. overnight. The resulting mixture was allowed to cool to ambient temperature and filtered through Celite to remove unsoluble precipitate. The filtrate was diluted with a mixed solvent of ethyl acetate and hexane (1:1, 200 ml), washed with brine (×2) and dried over anhydrous sodium sulfate. After removal of the solvent, the residue was solidified. The yellow solid was recrystallized from ethyl acetate and hexane to give desired compound (2.3 g).

後処理

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered through Celite
  3. customto remove unsoluble precipitate
  4. additionThe filtrate was diluted with a mixed solvent of ethyl acetate and hexane (1:1, 200 ml)
  5. washwashed with brine (×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the solvent
  8. customThe yellow solid was recrystallized from ethyl acetate and hexane

出典と根拠

ORDレコード
ord-465047e65b474da798367bf6c1f29529
出典データセット
uspto-grants-2002_03
特許番号
US06355799B1

反応ノート

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