Imidazole → HCID 87086952, compound

HRID 1095176Notes

Reaction equation

HRID 1095176 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].N1C=CN=C1.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].C(=O)(O)[O-].[Na+].C(Cl)[Cl:30]>>[Cl:30][C:3]1[CH:2]=[CH:9][C:6]([CH:7]=[O:8])=[C:5]([O:10][Si:20]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22])[CH:4]=1

Participants

6

Reactant 5

HCID 795Imidazole2×HCID 6344DichloromethaneHCID 124815-Chloro-salicylaldehydeHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 87086952HCID 87086952, compound

Procedure

To a stirred solution of 5-chloro-2-hydroxy-benzaldehyde (Aldrich, 7.83 g, 50 mmol) in methylene chloride (150 mL) were added imidazole (Aldrich, 3.72 g, 54.6 mmol) and tert-butyl-dimethyl-chloro-silane (Aldrich, 7.84 g, 52 mmol). The mixture was stirred at room temperature for 5 hrs. A second portion of imidazole (1.2 g) was added and mixture was stirred for 1 hr. The mixture was then poured into saturated sodium bicarbonate solution (150 mL). The organic layer was separated and the aqueous layer was extracted with methylene chloride (2×50 mL). The combined extracts were washed with water, brine and dried over magnesium sulfate. Removal of the solvent gave an off white solid. 13.62 g.

Workup

  1. stirringmixture was stirred for 1 hr
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with methylene chloride (2×50 mL)
  4. washThe combined extracts were washed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customRemoval of the solvent
  7. customgave an off white solid

Sources & evidence

ORD record
ord-1115cf3e0d4c409cb9094274d94694d8
Source dataset
uspto-grants-2012_03
Patent number
US08134001B2

Reaction notes

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