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Hydrochloric Acid → N-Tosylindole

HRID 2042940
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HRID 2042940 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[S:12](Cl)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13].Cl>CN(C=O)C>[S:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)([C:15]1[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 798IndoleHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydride

생성물 1

HCID 10956616N-Tosylindole수율 84%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of indole 81 (10 g, 85 mmol) in DMF (50 mL) at 0° C. was added NaH (60% dispersion in mineral oil 4 g) and tosylchloride (24 g, 128 mmol) portionwisely. And the reaction mixture was stirred at room temperature for 2 h. The resulting solution was acidified with 2.0 M HCl, and organic layer was extracted with Et2O. After evaporating the volatile material with reduced pressure, the residue was purified by silica column chromatography to obtain titled compound 82 (19 g, 84%).

후처리

  1. extractionwas extracted with Et2O
  2. customAfter evaporating the volatile material with reduced pressure
  3. customthe residue was purified by silica column chromatography

출처 및 근거

ORD 기록
ord-4f5fb899a43c4bef9347386cee446600
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08586550B2

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