Imidazole → HCID 70146468, compound

HRID 1598914Notes

Reaction equation

HRID 1598914 reaction equation
P(Cl)(Cl)(Cl)=O.N1[CH:10]=[CH:9]N=C1.C(OC([C:17]1[CH:18]=[C:19]([NH:23][C:24](=[O:30])NCC(O)=O)[CH:20]=[CH:21][CH:22]=1)=O)C=C.NC1[CH:45]=[CH:44][CH:43]=[CH:42][C:33]=1[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35].[C:46](=O)(O)[O-:47].[Na+].[CH3:51][C:52]([N:54]([CH3:56])C)=[O:53]>C(OCC)(=O)C.O>[CH2:46]([O:47][C:24]([N:23]([C:19]1[CH:18]=[CH:17][CH:22]=[CH:21][CH:20]=1)[CH2:51][C:52]([NH:54][C:56]1[CH:45]=[CH:44][CH:43]=[CH:42][C:33]=1[C:34]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:35])=[O:53])=[O:30])[CH:9]=[CH2:10]

Participants

9

Reactant 6

HCID 795ImidazoleHCID 24813Phosphorus oxychlorideHCID 31374Dimethylacetamide3×HCID 760802-AminobenzophenoneHCID 516892Sodium BicarbonateHCID 18930641HCID 18930641, compound

Product 1

HCID 70146468HCID 70146468, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To DMA (40 ml) are added phosphorous oxychloride (2.07 ml, 22.64 mmol) and imidazole (1.54 g, 22.64 mmol) with stirring and under cooling. A solution of (3-allyloxycarbonylphenyl)ureidoacetic acid (3.0 g, 10.78 mmol) in dimethylacetamide (10 ml) is added dropwise and the mixture is stirred for 10 minutes under ice-cooling. Then, a solution of 2-aminobenzophenone (2.34 g, 11.86 mmol) in DMA (5 ml) is added dropwise. The reaction solution is stirred at 50° C. for 5.5 hours. After allowing to cool, water and ethyl acetate are added to the reaction solution to adjust the pH to 9 with an aqueous saturated sodium bicarbonate solution, and the aqueous layer is extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue is crystallized from toluene to obtain the objective compound (3.63 g). Yield 74%.

Workup

  1. temperatureunder cooling
  2. stirringthe mixture is stirred for 10 minutes under ice-
  3. temperaturecooling
  4. stirringThe reaction solution is stirred at 50° C. for 5.5 hours
  5. temperatureto cool
  6. extractionthe aqueous layer is extracted with ethyl acetate
  7. washThe organic layer is washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue is crystallized from toluene

Sources & evidence

ORD record
ord-5dfd9393d92d44a6b07c88f33276166c
Source dataset
uspto-grants-1998_04
Patent number
US05739162

Reaction notes

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