Hydrochloric Acid → 1-Adamantan-2-yl-4-benzyl-5-isopropyl-1,3-dihydro-imidazol-2-one

HRID 1092316Notes

Reaction equation

HRID 1092316 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([NH:14][CH:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16](=O)[CH:17]([CH3:19])[CH3:18])=[O:13])[CH2:8]2.Cl.[Na+].[Cl-]>C1COCC1>[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[C:16]([CH:17]([CH3:19])[CH3:18])=[C:15]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:14][C:12]1=[O:13])[CH2:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 57495623HCID 57495623, compound

Product 1

HCID 249655011-Adamantan-2-yl-4-benzyl-5-isopropyl-1,3-dihydro-imidazol-2-oneYield 18.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Adamantan-2-yl-3-(1-benzyl-3-methyl-2-oxo-butyl)-urea (100 mg) was dissolved in dry THF (2 mL) and treated with 25% HCl (5 mL) at 60° C. for 3.5 hours. The mixture was cooled, poured into ice cold 3M NaOH, saturated with NaCl. The mixture was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography using a gradient of 10 to 40% ethyl acetate in heptane as an eluent. Fractions containing the desired material were combined and evaporated to give 1-adamantan-2-yl-4-benzyl-5-isopropyl-1,3-dihydro-imidazol-2-one as a white foam (18 mg). MS (EI): 350.3 (M+).

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. additionFractions containing the desired material
  9. customevaporated

Sources & evidence

ORD record
ord-4ba927c375f644f4b85804ddc2f7d578
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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