Imidazole → 4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenesulfonamide

HRID 351122노트

반응식

HRID 351122 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[Si:12]([O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:4][CH:3]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 74093p-Hydroxybenzenesulfonamide

생성물 1

HCID 210912414-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]benzenesulfonamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

4-Hydroxyphenylsulfonamide (3.46 g, 20 mmol) is dissolved in DMF (40 mL) and treated with tert-butyl-dimethylsilylchloride (3.31 g, 22.0 mmol) and imidazole (1.50 g, 22.0 mmol) at room temperature. After 20 hr, the reaction mixture is diluted with EtOAc (100 mL) and washed with 1.0 N HCl (2×50 mL). The organic phase is dried (MgSO4), filtered, and concentrated to yield an oil. The crude oil is purified by Biotage column chromatography (40M SiO2 column, eluted at 75 mL/min with 1:1 hexanes:EtOAc). A white solid is obtained (4.24 g, 15.4 mmol, 77%). ESI-MS m/e 288.1 (M++H); mp 117–118° C.; 1H NMR (CDCl3) δ 7.78 (d, 2H), 6.89 (d, 2H), 4.86 (br s, 2H), 0.97 (s, 9H), 0.20 (s, 6H).

후처리

  1. washwashed with 1.0 N HCl (2×50 mL)
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto yield an oil
  6. customThe crude oil is purified by Biotage column chromatography (40M SiO2 column, eluted at 75 mL/min with 1:1 hexanes:EtOAc)
  7. customA white solid is obtained (4.24 g, 15.4 mmol, 77%)

출처 및 근거

ORD 기록
ord-1b142715f9aa40fabd7b72af0a13d060
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183320B2

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