Imidazole → HCID 13592049, compound

HRID 2350981Notes

Reaction equation

HRID 2350981 reaction equation
[OH:1][C:2]1[C:3]([CH3:19])=[C:4]([CH3:18])[C:5]2[O:9][CH:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:7][C:6]=2[C:16]=1[CH3:17].N1C=CN=C1.[Si:25](Cl)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].O>CN(C)C=O>[Si:25]([O:1][C:2]1[C:3]([CH3:19])=[C:4]([CH3:18])[C:5]2[O:9][CH:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:7][C:6]=2[C:16]=1[CH3:17])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 13592047HCID 13592047, compound

Product 1

HCID 13592049HCID 13592049, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.6 g of 5-hydroxy-4,6,7-trimethyl-2-phenyl-1,3-benzoxathiole, 1.3 g of imidazole and 2.9 g of t-butyldimethylsilyl chloride were dissolved in 20 ml of dimethylformamide, and the mixture was reacted for 24 hours at room temperature. At the end of this time, the reaction mixture was poured into water. The separated product was extracted with benzene, and the extract was washed with a 5% w/v aqueous solution of ammonia and then with water and dried over anhydrous sodium sulfate. The solvent was evaporated off and the product thus obtained was purified by silica gel column chromatography. From the fraction eluted with a 10:1 by volume mixture of cyclohexane and benzene were obtained 3.1 g of the title compound, melting at 95°-98° C.

Workup

  1. customthe mixture was reacted for 24 hours at room temperature
  2. extractionThe separated product was extracted with benzene
  3. washthe extract was washed with a 5% w/v aqueous solution of ammonia
  4. dry with materialwith water and dried over anhydrous sodium sulfate
  5. customThe solvent was evaporated off
  6. customthe product thus obtained
  7. customwas purified by silica gel column chromatography
  8. washFrom the fraction eluted with a 10:1 by volume mixture of cyclohexane

Sources & evidence

ORD record
ord-e761b6575e2141a99c8736d3805d5ec0
Source dataset
uspto-grants-1989_10
Patent number
US04871762

Reaction notes

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