Imidazole → HCID 86667608, compound

HRID 85330Notes

Reaction equation

HRID 85330 reaction equation
[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([N:17]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:32]([Si:36](Cl)([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:35])([CH3:34])[CH3:33].O>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:16]=[C:15]([N:17]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:18][CH2:19][CH2:20][CH2:21][O:22][Si:36]([C:32]([CH3:35])([CH3:34])[CH3:33])([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:14]=[CH:13][C:10]=1[CH:11]=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 866676092-Benzyloxy-4-[butyl(4-hydroxybutyl)amino]benzaldehyde

Product 1

HCID 86667608HCID 86667608, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 20 ml of N,N-dimethylformamide were dissolved 1.63 g (4.59 mmol) of 2-benzyloxy-4-[butyl(4-hydroxybutyl)amino]benzaldehyde and 1.2 g (17.63 mmol) of imidazole. To this mixture, 1.27 g (4.62 mmol) of tert-butylchlorodiphenylsilane was added dropwise with stirring at room temperature. The mixture was stirred for 2 hours. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, and drying over anhydrous sodium sulfate were performed. The residue was purified by silica gel column chromatography to give 2.08 g of a colorless oily matter (yield: 76.5%).

Workup

  1. stirringThe mixture was stirred for 2 hours
  2. washwashing with a saturated saline solution
  3. dry with materialdrying over anhydrous sodium sulfate
  4. customThe residue was purified by silica gel column chromatography
  5. customto give 2.08 g of a colorless oily matter (yield: 76.5%)

Sources & evidence

ORD record
ord-787c9249ee1c4bd3b87bf030626e14db
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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