Water → Fluquazone

HRID 1395146ノート

反応式

HRID 1395146 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 219069Fluquazone収率 51.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88cd8204b98e4ca8850b4ef6d032fc28
出典データセット
uspto-grants-1980_05
特許番号
US04202895

反応ノート

読み込み中…