Imidazole → HCID 14802197, compound

HRID 2351007Notes

Reaction equation

HRID 2351007 reaction equation
[OH:1][C:2]1[C:3]([CH3:13])=[C:4]([CH3:12])[C:5]2[O:9][CH2:8][S:7][C:6]=2[C:10]=1[CH3:11].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]>CN(C)C=O>[Si:19]([O:1][C:2]1[C:3]([CH3:13])=[C:4]([CH3:12])[C:5]2[O:9][CH2:8][S:7][C:6]=2[C:10]=1[CH3:11])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13592053HCID 13592053, compound

Product 1

HCID 14802197HCID 14802197, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.84 g of 5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 64) was dissolved in 5 ml of dimethylformamide, and then 0.58 g of imidazole and 1.29 g of t-butyldimethylsilyl chloride were added to the resulting solution. The mixture was then stirred for 7 hours at 50° C., after which it was allowed to stand overnight at room temperature. The solvent was then distilled off under reduced pressure, and the residue was extracted with benzene. The extract was washed with a saturated aqueous solution of sodium bicarbonate and with water, and then dried over anhydrous sodium sulfate. The solvent was then distilled off. The resulting residue was subjected to column chromatography through 40 g of silica gel eluted with hexane and with mixtures of hexane and benzene ranging from 10:1 to 2:1 by volume, to yield 1.26 g of the title compound as a colorless oily substance.

Workup

  1. waitto stand overnight at room temperature
  2. distillationThe solvent was then distilled off under reduced pressure
  3. extractionthe residue was extracted with benzene
  4. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate and with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off
  7. washeluted with hexane and with mixtures of hexane and benzene ranging from 10:1 to 2:1 by volume

Sources & evidence

ORD record
ord-c679d4af40ca4223b2738945ee6be579
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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