Acetic Acid → N-(3-Methylphenyl)urea

HRID 963520Notes

Reaction equation

HRID 963520 reaction equation
C1(C2C3C=CC=CC=3NC(=O)C([NH:20][C:21]([NH:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([CH3:30])[CH:25]=3)=[O:22])N=2)CCCCCC1.BrCC(N1CC2CCC(CC2)C1)=O.[H-].[Na+].C(O)(=O)C>CN(C)C=O>[CH3:30][C:26]1[CH:25]=[C:24]([NH:23][C:21](=[O:22])[NH2:20])[CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 21701395N-bromomethylcarbonyl-3-azabicyclo[3.2.2]nonaneHCID 135829363N-[(3RS)-5-cycloheptyl-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea

Product 1

HCID 6142N-(3-Methylphenyl)ureaYield 237.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[(3RS)-5-cycloheptyl-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.102 g) and N-bromomethylcarbonyl-3-azabicyclo[3.2.2]nonane (0.079 g) in dry N,N-dimethylformamide (10 ml) was added sodium hydride (0.011 g of a 63.8% dispersion in mineral oil) at 5°-10° C. The mixture was stirred at the same temperature for 30 minutes and then at ambient temperature overnight. The resultant mixture was treated with 0.1 g of acetic acid at room temperature for 30 minutes and then concentrated in vacuo. The residue was disolved with ethyl acetate (100 ml) and washed with saturated sodium hydrogen carbonate aqueous solution (20 ml) and a brine (20 ml). The organic layer was dried over magnesium sulfate. Filtration and evaporation gave a crude product. The crude product was purified by column chromatography on silica gel with chloroform and a mixture of chloroform and ethyl acetate (5:1) as eluents to afford N-[(3RS)-1-[(3-azabicyclol3.2.2]non-3-yl)carbonylmethyl]-5-cycloheptyl-2,3-dihydro-2-oxo-1H-1,4-benzodiazepin-3-yl]-N'-(3-methylphenyl)urea (0.090 g).

Workup

  1. customat ambient temperature
  2. customovernight
  3. concentrationconcentrated in vacuo
  4. washwashed with saturated sodium hydrogen carbonate aqueous solution (20 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationFiltration and evaporation
  7. customgave a crude product
  8. customThe crude product was purified by column chromatography on silica gel with chloroform
  9. additiona mixture of chloroform and ethyl acetate (5:1) as eluents

Sources & evidence

ORD record
ord-4f60d0453eef4bdab80956bb0ce2120a
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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