Imidazole → HCID 18707383, compound

HRID 1421995Notes

Reaction equation

HRID 1421995 reaction equation
N1C=CN=C1.[C:6]([Si:10]([CH3:13])([CH3:12])Cl)([CH3:9])([CH3:8])[CH3:7].[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]([OH:37])=[C:33]([C:38]([O:40][CH3:41])=[O:39])[CH:32]=3)[N:30]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[CH3:15].C(OCC)(=O)C>CN(C)C=O>[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:37][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([CH3:13])[CH3:12])=[C:33]([C:38]([O:40][CH3:41])=[O:39])[CH:32]=3)[N:30]=2)[CH:20]=[CH:21][C:22]=1[O:23][CH2:24][CH3:25])[CH3:15]

Participants

6

Reactant 4

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

Product 1

HCID 18707383HCID 18707383, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.23 g of imidazole and 4.85 g of tert-butyldimethylchlorosilane 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-tert-butyldimethylsilyloxyphenyl)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-0b82facb4fb74c90a330af8795401ca7
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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