1,3-Dimethyl-2-imidazolidinone → HCID 136331481, compound

HRID 1587740Notes

Reaction equation

HRID 1587740 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])O[CH2:13][CH3:14].CN1CCN(C)C1=O.[N+:25]([N:28]=[C:29]1[NH:33]C[CH2:31][NH:30]1)([O-:27])=[O:26]>S(=O)(=O)(O)O.C(OCC)(=O)C>[CH3:9][C:8]([C:5]1[CH:6]=[CH:7][C:2]([N:1]=[CH:31][N:30]2[CH2:14][CH2:13][NH:33][C:29]2=[N:28][N+:25]([O-:27])=[O:26])=[CH:3][CH:4]=1)=[O:10]

Participants

7

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7468p-AminoacetophenoneHCID 53630039EthylorthoformateHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 136331481HCID 136331481, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5.0 g of p-aminoacetophenone. 6.6 g of ethyl orthoformate, 5 ml of 1,3-dimethyl-2-imidazolidinone and 0.03 g of concentrated sulfuric acid was placed in a reactor equipped with Dean's stark tube and agitated at 140° C. for about 10 minutes, followed by further addition of 5.8 g of nitroiminoimidazolidine and agitation at 160° C. for 1 hour. The reaction mixture was poured into 200 ml of a saturated saline solution, to which 150 ml of ethyl acetate was added. The resultant crystals were collected by filtration, and dried to give 5.4 g of 1-(4-methylcarbonyl-phenyliminomethyl)-2-nitroiminoimidazolidine.

Workup

  1. customequipped with Dean's stark tube
  2. additionwas added
  3. filtrationThe resultant crystals were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-892d5c7f0fc544b9b232cf07c8a14e7f
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

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