Imidazole → HCID 178466124, compound

HRID 263605Notes

Reaction equation

HRID 263605 reaction equation
N1C=CN=[CH:2]1.[C:6]([Si:10]([CH3:13])(C)Cl)(C)(C)C.[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([C:26]2[S:27][CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][C:34](O)=[C:33]([C:38](OC)=O)[CH:32]=3)[N:30]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[CH3:15].[C:42]([O:45][CH2:46]C)(=[O:44])[CH3:43].CN(C)[CH:50]=[O:51]>>[CH2:14]([O:16][C:17]1[CH:18]=[C:19]([C:26]2[S:27][CH:28]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([C:33]([CH3:38])([CH3:32])[CH3:2])=[C:43]([C:42]([O:45][CH3:46])=[O:44])[C:50]=3[O:51][SiH:10]([CH3:13])[CH3:6])[N:30]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[CH3:15]

Participants

6

Reactant 5

HCID 795ImidazoleHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 18707277HCID 18707277, compound

Product 1

HCID 178466124HCID 178466124, compound

Procedure

5.23 g of imidazole and 4.85 g of tertbutyldimethylchlorosilane were added, in this order, to a suspension of 4.02 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxyphenyl)thiazole in 60 ml of dimethylformamide at room temperature. The mixture was stirred at the same temperature for 4 hours. To the reaction mixture were added 100 ml of ice water and 200 ml of ethyl acetate. The organic layer was separated, washed with 100 ml of water and 50 ml of a saturated aqueous sodium chloride solution in this order, dried over anhydrous magnesium sulfate and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate =10/1) to obtain 5.14 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-tertbutyldimethylsilyloxyphenyl)thiazole.

Workup

  1. customThe organic layer was separated
  2. washwashed with 100 ml of water and 50 ml of a saturated aqueous sodium chloride solution in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationsubjected to distillation
  5. customto remove the solvent
  6. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate =10/1)

Sources & evidence

ORD record
ord-da311e7d1a234b6b9c645b6173cc39cc
Source dataset
uspto-grants-1997_07
Patent number
US05643932

Reaction notes

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