Imidazole → HCID 54284754, compound

HRID 2291292Notes

Reaction equation

HRID 2291292 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].N1C=CN=C1.[C:16]1([Si:22](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([O:7][Si:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:23]([CH3:26])([CH3:24])[CH3:25])=[O:6]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 74203-Hydroxybenzoic AcidHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 54284754HCID 54284754, compoundYield 52.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To stirred solution of 50.4 g of 3-hydroxybenzoic acid in 200 ml of dry dimethylformamide at 0° C. was added 24.85 g of imidazole, followed by 100 g of diphenyl-(2-methylprop-2-yl)silyl chloride. The mixture was stirred at room temperature for 16 hours, and partitioned between ethyl acetate and cold water. The organic layer was washed with water, with an aqueous potassium hydrogen carbonate solution and with brine, was dried over anhydrous magnesium sulphate and evaporated to dryness. The resulting white solid was slurried in dry chloroform and filtered to afford 72 g of the title compound.

Workup

  1. custompartitioned between ethyl acetate and cold water
  2. washThe organic layer was washed with water, with an aqueous potassium hydrogen carbonate solution and with brine
  3. dry with materialwas dried over anhydrous magnesium sulphate
  4. customevaporated to dryness
  5. filtrationfiltered

Sources & evidence

ORD record
ord-9e8ffa4e6b3c4722a96061e80dbc1af1
Source dataset
uspto-grants-1989_01
Patent number
US04795748

Reaction notes

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