Diisopropylethylamine → 5-Benzyl-3-(4-bromophenyl)-1,3-oxazolan-2-one

HRID 897627

반응식

HRID 897627 반응식
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][CH2:7][CH:8]([OH:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>ClCCl>[CH2:9]([CH:8]1[O:16][C:29](=[O:31])[N:6]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:18][CH:17]=2)[CH2:7]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 223472001-(4-Bromoanilino)-3-phenyl-2-propanol

생성물 1

HCID 223467395-Benzyl-3-(4-bromophenyl)-1,3-oxazolan-2-one수율 121.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

A solution containing 1-(4-bromoanilino)-3-phenyl-2-propanol (1.90 g, 0.00621 mol), N,N-diisopropylethylamine (2.48 g, 0.0193 mol) and N,N-dimethylaminopyridine (0.152 g, 0.00124 mol) in anhydrous dichloromethane (64 mL) was cooled to 0° C. and the solution of triphosgene (0.92 g, 0.0031 mol) in anhydrous dichloromethane (16 mL) was added dropwise. The reaction mixture was slowly warmed up to ambient temperature while stirring under an atmosphere of nitrogen for 18 hours. The organic phase was washed with saturated solution of sodium bicarbonate in water (70 mL), brine (60 mL) and dried with magnesium sulfate. The solvent was removed under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (1:5) as mobile phase to yield 5-benzyl-3-(4-bromophenyl)-1,3-oxazolan-2-one (1.25 g, 0.00377 mol) as a white solid.

후처리

  1. temperatureThe reaction mixture was slowly warmed up to ambient temperature
  2. washThe organic phase was washed with saturated solution of sodium bicarbonate in water (70 mL), brine (60 mL)
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by flash chromatography on silica

출처 및 근거

ORD 기록
ord-02b8f9dae8824ecb9b9fa269f4090091
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06921763B2

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