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Tin tetrachloride → Ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate

HRID 2423528
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반응식

HRID 2423528 반응식
[Sn](Cl)(Cl)(Cl)Cl.[Br:6][C:7]1[CH:8]=[C:9]([CH2:13][CH2:14][NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH:10]=[CH:11][CH:12]=1.Cl[CH:26](SC)[C:27]([O:29][CH2:30][CH3:31])=[O:28]>ClCCl.ClCCCl>[Br:6][C:7]1[CH:8]=[C:9]2[C:10](=[CH:11][CH:12]=1)[CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:15]([S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH2:14][CH2:13]2.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:8]=1[CH:26]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:15]([S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:18])=[O:17])[CH2:14][CH2:13]2
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참가 물질

7

반응물 3

HCID 24287Tin tetrachlorideHCID 10877535Ethyl 2-chloro-2-(methylsulfanyl)acetateHCID 59321588N-[2-(3-bromophenyl)ethyl]benzenesulfonamide

생성물 2

HCID 59321554Ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate수율 79%HCID 59321590Ethyl 8-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate
수율 19%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

Tin(IV)chloride (6.67 mL of a 1 M solution in dichloromethane, 6.67 mmol) was added to N-[2-(3-bromophenyl)ethyl]benzenesulfonamide (1.08 g, 3.17 mmol) and ethyl chloro(methylthio)acetate (1.07 g, 6.35 mmol) in 1,2-dichloroethane (11 mL) under argon and the reaction was heated at reflux for 3 hours. After cooling, the mixture was poured into ice water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:4 ethyl acetate:hexanes to give 1.07 g (79%) of ethyl 6-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate and 255.6 mg (19%) of ethyl 8-bromo-2-(phenylsulfonyl)-1,2,3,4-tetrahydro-1-isoquinolinecarboxylate as oils.

후처리

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium bicarbonate and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with 1:4 ethyl acetate

출처 및 근거

ORD 기록
ord-cf374c60b32f45cfa6cf4a4d05e4f2ab
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960552B2

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