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Imidazole → N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide

HRID 1468945
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HRID 1468945 반응식
[OH:1][CH2:2][C:3]1[C:8]([S:9][CH3:10])=[CH:7][C:6]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:5]([I:16])[CH:4]=1.N1C=CN=C1.[Si:22](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl.CN(C=O)C>[Si:22]([O:1][CH2:2][C:3]1[C:8]([S:9][CH3:10])=[CH:7][C:6]([NH:11][S:12]([CH3:15])(=[O:13])=[O:14])=[C:5]([I:16])[CH:4]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 89814728N-(4-(hydroxymethyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide

생성물 1

HCID 89814652N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 6344
Dichloromethane
용매
2회

실험 절차

To a stirred solution of N-(4-(hydroxymethyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide (6.4 g, 17.2 mmol) and imidazole (1.76 g, 25.8 mmol) in CH2Cl2 (100 mL) and DMF (50 mL) at 0° C. was added tert-butyldiphenylsilyl chloride (5.8 mL, 22.4 mmol). The mixture was allowed to stir at rt overnight. The mixture was diluted with CH2Cl2 (100 mL), washed with 1N HCl solution, sat. aq. NaHCO3 and brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford N-(4-(((tert-butyldiphenylsilyl)oxy)methyl)-2-iodo-5-(methylthio)phenyl)methanesulfonamide. It was used for next step without further purification.

후처리

  1. washwashed with 1N HCl solution, sat. aq. NaHCO3 and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9fa622e477bb418cb066d96d6055b21e
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006245B2

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