Nitrobenzene → 1,3-Dihydro-4-(3,4-methylenedioxybenzoyl)-5-methyl-2H-imidazol-2-one

HRID 1995666Notes

Reaction equation

HRID 1995666 reaction equation
[CH3:1][C:2]1[NH:3][C:4](=[O:7])[NH:5][CH:6]=1.[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[CH2:21]1[O:32][C:31]2[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][C:23]=2[O:22]1>>[CH2:21]1[O:32][C:31]2[CH:30]=[CH:29][C:25]([C:26]([C:6]3[NH:5][C:4](=[O:7])[NH:3][C:2]=3[CH3:1])=[O:27])=[CH:24][C:23]=2[O:22]1

Participants

5

Reactant 4

HCID 7416NitrobenzeneHCID 709351,3-dihydro-4-methyl-2H-imidazol-2-oneHCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 128560281,3-Dihydro-4-(3,4-methylenedioxybenzoyl)-5-methyl-2H-imidazol-2-one

Procedure

To 5.13 g. of 1,3-dihydro-4-methyl-2H-imidazol-2-one and 7.98 g. of anhydrous aluminum chloride in 80 ml. of nitrobenzene is added dropwise 10.60 g. of 3,4-methylenedioxybenzoyl chloride and the mixture is poured on 500 ml. of 2N-HCl and ice, washed 3 times with ethyl ether, the resulting solid is collected to give the title compound. M.p. 293°-296° C. (dec.).

Workup

  1. washof 2N-HCl and ice, washed 3 times with ethyl ether
  2. customthe resulting solid is collected

Sources & evidence

ORD record
ord-853f83bb6c5543bf80368dcc231d3499
Source dataset
uspto-grants-1983_09
Patent number
US04405635

Reaction notes

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