Imidazole → HCID 68422308, compound

HRID 1515374Notes

Reaction equation

HRID 1515374 reaction equation
C(Cl)Cl.Cl[Si:5]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].[OH:12][CH2:13][CH2:14]/[C:15](=[CH:25]\[S:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)/[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].N1C=CN=C1>O>[Si:5]([O:12][CH2:13][CH2:14]/[C:15](=[CH:25]\[S:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)/[C:16]([NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17])([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344Dichloromethane2×HCID 28928tert-Butyldimethylsilyl chlorideHCID 67426931HCID 67426931, compound

Product 1

HCID 68422308HCID 68422308, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 ml of methylene chloride solution including 0.79 g of chloro t-butyl dimethylsilane was dropped into 6 ml of methylene chloride solution including 1.20 g of (E)-4-hydroxy-N-phenyl-2-(phenylthiomethylene)butanamide and 0.63 g of imidazole at room temperature. The resulting solution was stirred at room temperature for 2 hours and added with water, then filtered using ethyl acetate. The organic layer was washed with water 3 times, then washed with brine, and dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.63 g of the title compound.

Workup

  1. customat room temperature
  2. filtrationfiltered
  3. washThe organic layer was washed with water 3 times
  4. washwashed with brine
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e78dcc867b6d43f099dcd6463c118bf7
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

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