Imidazole → HCID 22382417, compound

HRID 1349453Notes

Reaction equation

HRID 1349453 reaction equation
[OH:1][CH2:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6].N1C=CN=C1.[C:20]([Si:24]([CH3:27])([CH3:26])Cl)([CH3:23])([CH3:22])[CH3:21].O>CN(C)C=O>[Si:24]([O:1][CH2:2][C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[C:5]([N:7]([O:9][CH3:10])[CH3:8])=[O:6])([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 22382443HCID 22382443, compound

Product 1

HCID 22382417HCID 22382417, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of phthalide (26.8 g) in methylene chloride (600 ml) were successively added N,O-dimethylhydroxylamine hydrochloride (58.5 g) and aluminum chloride (40.0 g) under ice-cooling, and triethylamine (139 ml) was added dropwise over 40 min. The mixture was stirred at room temperature for 12 hr. The reaction mixture was poured into diluted hydrochloric acid, and the organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 2-hydroxymethyl-N-methoxy-N-methylbenzamide. The obtained 2-hydroxymethyl-N-methoxy-N-methylbenzamide was dissolved in N,N-dimethylformamide (300 ml), and imidazole (9.53 g) and tert-butyldimethylchlorosilane (21.1 g) were added. The mixture was stirred at room temperature for 3.5 hr and the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentration under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (42.0 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate, and concentration under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:3)

Sources & evidence

ORD record
ord-b01ec3b39c43490a801b50d6b03dfa27
Source dataset
uspto-grants-2007_05
Patent number
US07211685B2

Reaction notes

Loading…