HCID 22456838, compound → HCID 22456853, compound

HRID 2186516Notes

Reaction equation

HRID 2186516 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, washed 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
  5. customThe residue was 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. washwashed with ethylacetate and DIPE
  11. customdried

Sources & evidence

ORD record
ord-f93c490bf9a44c24b990b5671043809f
Source dataset
uspto-grants-2002_06
Patent number
US06403805B1

Reaction notes

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