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Ethylene Glycol → methyl 7-bromo-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate

HRID 587090
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HRID 587090 반응식
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13](=[O:15])[CH3:14])[CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=2[CH:20]=1.[CH2:21](O)[CH2:22][OH:23]>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][C:13]3([CH3:14])[O:23][CH2:22][CH2:21][O:15]3)[CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=2[CH:20]=1
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참가 물질

5

반응물 2

HCID 174Ethylene GlycolHCID 22329093methyl 7-bromo-1-(2-oxopropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate

생성물 1

HCID 22328896methyl 7-bromo-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate수율 68%

시약·촉매·용매 2

HCID 521998p-Toluenesulfonic acid monohydrate촉매HCID 1140Toluene
용매

실험 절차

A solution of methyl 7-bromo-1-(2-oxopropyl)-2,3-dihydro-1H-1-benzazepine-4-carboxylate (1.29 g), ethylene glycol (2.3 g) and p-toluenesulfonic acid monohydrate (36 mg) in toluene (10 ml) was heated to reflux for 3 days while removing water. After cooled to room temperature, an aqueous solution of sodium hydrogen carbonate was added to alkaline, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated and purified with column chromatography (ethyl acetate:hexane=1:4) to give methyl 7-bromo-1-[(2-methyl-1,3-dioxolan-2-yl)methyl]-2,3-dihydro-1H-1-benzazepine-4-carboxylate (992 mg).

후처리

  1. temperatureto reflux for 3 days
  2. customwhile removing water
  3. additionan aqueous solution of sodium hydrogen carbonate was added to alkaline
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was separated
  9. custompurified with column chromatography (ethyl acetate:hexane=1:4)

출처 및 근거

ORD 기록
ord-264cd707054a44768860930208aa4e8b
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06936602B1

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