Imidazole → HCID 67425928, compound

HRID 1515378Notes

Reaction equation

HRID 1515378 reaction equation
Cl[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(Cl)Cl.[OH:22][CH2:23][CH2:24][CH2:25]/[C:26](=[CH:36]\[S:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)/[C:27]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28].N1C=CN=C1>O>[Si:2]([O:22][CH2:23][CH2:24][CH2:25]/[C:26](=[CH:36]\[S:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)/[C:27]([NH:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:28])([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 94078tert-ButyldiphenylchlorosilaneHCID 67426036HCID 67426036, compound

Product 1

HCID 67425928HCID 67425928, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.87 g of chloro t-butyl diphenylsilane was dropped into 10 ml of methylene chloride solution including 1.64 g of (E)-5-hydroxy-N-phenyl-2-(phenylthiomethylene)pentanamide and 0.82 g of imidazole at room temperature. After stirring at room temperature for 2 hours, the resulting solution was added with water and extracted with ethyl acetate. The organic layer was washed 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 2.81 g the title compound.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed 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-2f7fcc79dce545d7be3e3474ed6ad84f
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

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