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Methanol → N-(8-Bromo-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

HRID 1643899
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HRID 1643899 반응식
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][C@@H:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2)#[N:2].CO.C([O-])([O-])=O.[Ca+2].[Br-:30].[Br-].[Br-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C([N+](CC)(CC)CC)C1C=CC=CC=1.C([N+](CC)(CC)CC)C1C=CC=CC=1>C1COCC1.C(Cl)Cl>[Br:30][C:11]1[CH:12]=[C:3]([C:1]#[N:2])[CH:4]=[C:5]2[C:10]=1[NH:9][CH2:8][CH:7]([NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH2:6]2
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참가 물질

7

반응물 4

HCID 887MethanolHCID 10112Calcium CarbonateHCID 66757946(S)-N-(6-Cyano-1,2,3,4-tetrahydro-quinolin-3-yl)-benzenesulfonamideHCID 86596066Benzyltriethylammonium tribromide

생성물 1

HCID 66757940N-(8-Bromo-6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide수율 77%

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of racemate 1G (323 mg, 1.03 mmol) in mixed solvents of MeOH (3 mL), CH2Cl2 (3 mL) and THF (3 mL) at RT was added CaCO3 (103 mg, 1.03 mmol), followed by benzyltriethylammonium tribromide (445 mg, 1.03 mmol). After addition, the mixture was stirred at RT for 45 min. The resultant precipitate was collected by filtration, washed with 0.2 N aqueous HCl, H2O, then dried to provide the title compound (311 mg, 77%) as a white solid.

후처리

  1. additionAfter addition
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with 0.2 N aqueous HCl, H2O
  4. customdried

출처 및 근거

ORD 기록
ord-45e711c1f9c444a19d24daf9069beae8
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119808B2

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