HCID 22456838, compound → HCID 22456853, compound

HRID 1604429Notes

Reaction equation

HRID 1604429 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([O:26][CH2:27][CH3:28])[CH2:12][N:13]2[CH:17]=[CH:16][N:15](CC3C=CC=CC=3)[C:14]2=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1([Li])C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([O:26][CH2:27][CH3:28])[CH2:12][N:13]2[CH:17]=[CH:16][NH:15][C:14]2=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 22456838HCID 22456838, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 22456853HCID 22456853, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (±)-1-[2-(3,4-dimethoxyphenyl)-2-ethoxyethyl]-1,3-dihydro-3-(phenylmethyl)-2H-imidazol-2-one (4.86 g) in THF (100 ml) was stirred at RT. Phenyllithium (1.278 g) was added dropwise and the mixture was stirred overnight at RT. The mixture was carefully poured out into ice/water (200 ml), then extracted three times with CH2Cl2 (150 ml). The separated organic layer was dried (MgSO4), filtered, and the solvent was evaporated The residue was purified by short column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5). The desired fractions were collected and the solvent was evaporated. The residue was crystallized from ethylacetate. The precipitate was filtered off, wased with ethylacetate and DIPE, then dried, yielding 0.1 g (3%) of (±)-1-[2(3,4-dimethoxyphenyl)-2-ethoxyethyl]-1,3-dihydro-2H-imidazol-2-one (comp. 15; mp. 133.6° C.).

Workup

  1. extractionextracted three times with CH2Cl2 (150 ml)
  2. dry with materialThe separated organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated The residue
  5. customwas purified by short column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5)
  6. customThe desired fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from ethylacetate
  9. filtrationThe precipitate was filtered off
  10. customdried

Sources & evidence

ORD record
ord-9dac0b8badc2404ba98505cd2a0c5791
Source dataset
uspto-grants-1999_11
Patent number
US05994376

Reaction notes

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