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Ethyl bromoacetate → 3-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

HRID 482770
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HRID 482770 반응식
[Br:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[NH:4][C:3]1=[O:13].[OH-].[K+].Br[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Br:1][CH:2]1[CH2:8][CH2:7][C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:3]1=[O:13]
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참가 물질

6

반응물 3

HCID 7748Ethyl bromoacetateHCID 14797Potassium HydroxideHCID 27571843-Bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one

생성물 1

HCID 133399633-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매
HCID 8028
Tetrahydrofuran
용매

실험 절차

3-Bromo-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one (300 mg) was added in one portion to a stirred suspension of potassium hydroxide (90 mg) and tetrabutylammonium bromide (40 mg) in tetrahydrofuran (10 ml) maintained at 0° under a nitrogen atmosphere. Stirring was continued for 5 minutes, then ethyl bromoacetate (200 mg) was added in one portion. The reaction mixture was allowed to warm to room temperature while stirring for an additional 3 hours. The tetrahydrofuran was removed under reduced pressure and the residue partitioned between water (5 ml) and ether (25 ml). The organic phase was washed with 2N hydrochloric acid (5 ml), dried over magnesium sulfate, and the solvent removed under reduced pressure to give 3-bromo-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]-benzazepin-2-one, m.p. 114°-116°.

후처리

  1. temperaturemaintained at 0° under a nitrogen atmosphere
  2. stirringwhile stirring for an additional 3 hours
  3. customThe tetrahydrofuran was removed under reduced pressure
  4. customthe residue partitioned between water (5 ml) and ether (25 ml)
  5. washThe organic phase was washed with 2N hydrochloric acid (5 ml)
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-d59d552b153e4fda92a71510b85cf9fe
출처 데이터셋
uspto-grants-1986_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04575503

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