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

HRID 351122Notes

Reaction equation

HRID 351122 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-1b142715f9aa40fabd7b72af0a13d060
Source dataset
uspto-grants-2007_02
Patent number
US07183320B2

Reaction notes

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