HCID 10093715, compound → HCID 10250894, compound

HRID 1073532Notes

Reaction equation

HRID 1073532 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:19])[N:3]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30]C)=[O:29]>Cl>[O:1]=[C:2]1[N:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:19])[N:3]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29]

Participants

3

Reactant 1

HCID 10093715HCID 10093715, compound

Product 1

HCID 10250894HCID 10250894, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of methyl 2,5-dioxo-3,4-diphenyl-1-imidazolidinenonanoate (3.00 g, 7 mmol) and 6N HCl solution (30 mL) was heated at reflux for 22 hours. The mixture was cooled, extracted with CH2Cl2 and the combined extracts washed with water and twice with saturated sodium chloride solution. After drying over sodium sulfate, the solvent was evaporated and the residue chromatographed on a column of silica gel using a mixture of hexanes and ethyl acetate (2:1) as eluent. Elution gave 2,5-dioxo-3,4-diphenyl-1-imidazolidinenonanoic acid (1.06 g, 36%) after recrystallization from a mixture of hexanes, diethyl ether and CH2Cl2 (6:2:2), mp 111.5°-112.5° C. Anal. Calcd. for C24H28N2O4 : C, 70.57: H, 6.91: N, 6.86. Found: C, 70.45: H, 7.05: N, 6.75%.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 22 hours
  3. temperatureThe mixture was cooled
  4. extractionextracted with CH2Cl2
  5. washthe combined extracts washed with water and twice with saturated sodium chloride solution
  6. dry with materialAfter drying over sodium sulfate
  7. customthe solvent was evaporated
  8. customthe residue chromatographed on a column of silica gel using
  9. additiona mixture of hexanes and ethyl acetate (2:1) as eluent
  10. washElution

Sources & evidence

ORD record
ord-68e09ef1defb4203bdb7d46d53b435ca
Source dataset
uspto-grants-1990_11
Patent number
US04970225

Reaction notes

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