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

HRID 1265386노트

반응식

HRID 1265386 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
55 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ecb1d7eb722a4c7ab785d46cfe9e565b
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06545161B2

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