Water → Fluquazone

HRID 1395146노트

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HRID 1395146 반응식
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=3)[NH:10][C:9](=[O:18])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[F:21][C:22]([F:26])([F:25])[CH2:23]I.O>CN(C)C=O>[F:21][C:22]([F:26])([F:25])[CH2:23][N:10]1[C:11]2[C:16](=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][C:9]1=[O:18]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 632046-Chloro-4-phenyl-2(1H)-quinazolinoneHCID 677091,1,1-Trifluoro-2-iodoethane

생성물 1

HCID 219069Fluquazone수율 51.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a suspension of 5.13 g of 4-phenyl-6-chloro-2(1H)-quinazolinone in 60 ml of dimethylformamide was added 0.85 g 62% sodium hydride, and the resulting mixture was stirred at 100° C. for 30 minutes. Thereafter, 10.0 g of 2,2,2-trifluoroethyl iodide was added and the mixture was stirred at 140° C. for 8 hours. After cooling, the reaction mixture was poured into 300 ml of water and the resulting mixture was extracted with chloroform. The chloroform layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The oily residue was absorbed on a silica gel column, eluted with chloroform to obtain 3.5 g of 1-(2,2,2-trifluoroethyl)-4-phenyl-6-chloro-2(1H)-quinazolinone which was recrystallized from ethanol to give pale yellow leaflets melting at 185.0°-186.0° C., and 2.0 g of 2-(2,2,2-trifluoroethoxy)-4-phenyl-6-chloroquinazoline which was recrystallized from ethanol to give pale yellow needles melting at 113.0°-114.0° C.

후처리

  1. stirringthe mixture was stirred at 140° C. for 8 hours
  2. temperatureAfter cooling
  3. extractionthe resulting mixture was extracted with chloroform
  4. washThe chloroform layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was absorbed on a silica gel column
  8. washeluted with chloroform

출처 및 근거

ORD 기록
ord-88cd8204b98e4ca8850b4ef6d032fc28
출처 데이터셋
uspto-grants-1980_05
특허 번호
US04202895

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