Benzene, 1-chloro-4-fluoro- → 1-Benzhydryl-3-(4-chlorophenoxy)azetane

HRID 974538노트

반응식

HRID 974538 반응식
[H-].[Na+].[C:3]1([CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:10]2[CH2:13][CH:12]([OH:14])[CH2:11]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].[Cl:23][C:24]1[CH:29]=[CH:28][C:27](F)=[CH:26][CH:25]=1>CN(C)C=O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([O:14][CH:12]2[CH2:13][N:10]([CH:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11]2)=[CH:26][CH:25]=1

참가 물질

6

반응물 4

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 24758Sodium hydrideHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 5974941-Benzhydryl-3-(4-chlorophenoxy)azetane수율 82.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
90 °C

실험 절차

A stirred slurry of 41.3 g (1.03 mole) of 60% sodium hydride (in mineral oil) in 500 ml of dry dimethylformamide under nitrogen atmosphere was heated to 50° C. and 22.5 g (0.94 mole) of 1-diphenylmethyl-3-azetidinol in 700 ml of dry dimethylformamide was added dropwise at a rate which maintained the temperature between 70°-80° C. and allowed a gentle evolution of hydrogen. After the addition was complete, the reaction mixture was stirred for 2 hr at 90° C., then 125 g (0.94 mole) of 1-chloro-4-fluorobenzene was added dropwise. The reaction mixture was stirred at 90° C. under nitrogen for 24 hr, then stirred an additional 24 hr while the reaction mixture cooled to ambient temperature. The reaction mixture was poured into 6 liter of ice water and the solid which formed was collected by filtration to yield 271 g of wet crude product. A sample was recrystallized for elemental analysis from ethanol, yielding a fine tan crystalline product in 82.4% yield, m.p. 113°-114° C.

후처리

  1. temperaturemaintained the temperature between 70°-80° C.
  2. additionAfter the addition
  3. stirringThe reaction mixture was stirred at 90° C. under nitrogen for 24 hr
  4. stirringstirred an additional 24 hr while the reaction mixture
  5. temperaturecooled to ambient temperature
  6. customthe solid which formed
  7. filtrationwas collected by filtration

출처 및 근거

ORD 기록
ord-a59d6d59c0e14d7bab136d1e6e1b0415
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068231

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