Benzenesulfonyl chloride → HCID 18765369, 화합물

HRID 1159862노트

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HRID 1159862 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH3:19])[N:14]([S:26]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:28])=[O:27])[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 7369Benzenesulfonyl chlorideHCID 2608005-Benzyloxy-6-methoxyindole

생성물 1

HCID 18765369HCID 18765369, 화합물수율 84%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 14798Sodium Hydroxide용매

실험 절차

To 5-benzyloxy-6-methoxyindole (5.0 g, 20 mmol), benzenesulfonyl chloride (5.2 g, 30 mmol) and tetrabutylammonium hydrogen sulfate (2.0 g, 6 mmol) DCM (200 mL) and 4M NaOH (50 mL) were added. The reaction mixture was allowed to stir at room temperature over night. The organic layer was collected and the aqueous phase was washed with DCM (2×30 mL). The combined organic layers were then washed with brine (2×50 mL). Drying, (MgSO4), filtration and evaporation afforded a brown oil. The product precipitated when adding diethyl ether. Recrystallization from MeOH afforded the title compound in 84% yield (6.55 g) as light yellow crystals. MS (ESI+) for C22H19NO4S m/z 394 (M+H)+.

후처리

  1. customThe organic layer was collected
  2. washthe aqueous phase was washed with DCM (2×30 mL)
  3. washThe combined organic layers were then washed with brine (2×50 mL)
  4. customDrying
  5. filtration, (MgSO4), filtration and evaporation
  6. customafforded a brown oil
  7. customThe product precipitated when
  8. additionadding diethyl ether
  9. customRecrystallization from MeOH

출처 및 근거

ORD 기록
ord-50a92435fe054cdebc3c57b3be45f1a9
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812017B2

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