Sodium Chloride → HCID 57495524, compound

HRID 1092306Notes

Reaction equation

HRID 1092306 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[NH:13][C:12]1=[O:19])[CH2:8]2.[H-].[Na+].Br[CH2:23][CH:24]1[CH2:26][CH2:25]1.[Na+].[Cl-]>CN(C=O)C>[CH:1]12[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH:2]1[N:11]1[CH:15]=[C:14]([CH:16]([CH3:17])[CH3:18])[N:13]([CH2:23][CH:24]3[CH2:26][CH2:25]3)[C:12]1=[O:19])[CH2:10]2

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 24964431HCID 24964431, compound

Product 1

HCID 57495524HCID 57495524, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Adamantan-2-yl-4-isopropyl-1,3-dihydro-imidazol-2-one (obtained in example 8, 100 mg) was dissolved in dry DMF under argon and sodium hydride (55% in mineral oil) was added. The mixture was allowed to stir for 45 minutes and then bromomethylcyclopropane (0.04 ml) was added drop by drop. Stirring was continued at RT for another 4 hours. The reaction mixture was poured into ice/water, saturated with NaCl and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and evaporated to give a residue that was purified by flash chromatography using a gradient of 10 to 80% ethyl acetate in heptane as an eluent. Fractions containing the desired material were combined and evaporated to give 1-adamantan-2-yl-3-cyclopropylmethyl-4-isopropyl-1,3-dihydro-imidazol-2-one as a colorless oil (87 mg). MS (ESI): 315.2 (MH+).

Workup

  1. stirringStirring
  2. waitwas continued at RT for another 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto give a residue that
  8. customwas purified by flash chromatography
  9. additionFractions containing the desired material
  10. customevaporated

Sources & evidence

ORD record
ord-e29ebc2754644866bb9ba0654fa4aa7a
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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