Ethyl Acetate → N-Methyl-3-[4-(4-nitrobenzyl)-2,5-dioxoimidazolidinylmethyl]benzamide

HRID 483369Notes

Reaction equation

HRID 483369 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][CH:9]2[C:13](=[O:14])[NH:12][C:11](=[O:15])[NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:19][C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([NH:25][CH3:26])=[O:24].C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH3:26][NH:25][C:23](=[O:24])[C:22]1[CH:27]=[CH:28][CH:29]=[C:20]([CH2:19][N:12]2[C:13](=[O:14])[CH:9]([CH2:8][C:7]3[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[NH:10][C:11]2=[O:15])[CH:21]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 104665795-[(4-Nitrophenyl)methyl]imidazolidine-2,4-dioneHCID 226602083-(chloromethyl)-N-methylbenzamide

Product 1

HCID 10068456N-Methyl-3-[4-(4-nitrobenzyl)-2,5-dioxoimidazolidinylmethyl]benzamideYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from step (a) (4.0 g), the product from step (b) (3.3 g) and anhy. K2CO3 (2.55 g) were taken up in DMF (25 ml) and stirred at room temperature for 60 hours. The mixture was poured with vigorous stirring into ice-water (175 ml) to give an oily precipitate. Ethyl acetate was added and stirring continued for 1 hour to solidify the precipitate. The latter was filtered off, washed with water, ethyl acetate and ether, and dried to give the desired product as a peach-coloured solid (4.5 g).

Workup

  1. additionThe mixture was poured
  2. customto give an oily precipitate
  3. stirringstirring
  4. waitcontinued for 1 hour
  5. filtrationThe latter was filtered off
  6. washwashed with water, ethyl acetate and ether
  7. customdried

Sources & evidence

ORD record
ord-492dce69b7e9401193ac8693905e0858
Source dataset
uspto-grants-1993_07
Patent number
US05225431

Reaction notes

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