1,3-Dimethyl-2-imidazolidinone → HCID 136331480, compound

HRID 1587739Notes

Reaction equation

HRID 1587739 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].C([O-])([O-])O[CH2:12][CH3:13].[N+:16]([N:19]=[C:20]1[NH:24]C[CH2:22][NH:21]1)([O-:18])=[O:17].CN1CCN(C)C1=O>S(=O)(=O)(O)O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([N:5]=[CH:22][N:21]2[CH2:13][CH2:12][NH:24][C:20]2=[N:19][N+:16]([O-:18])=[O:17])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

7

Reactant 4

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 72483,4-DimethylanilineHCID 53630039EthylorthoformateHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 136331480HCID 136331480, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 60.6 g of 3,4-dimethylaniline, 200 g of ethyl orthoformate and 0.05 g of sulfuric acid was placed in a reactor equipped with Dean's stark tube and agitated at 140° to 165° C. for about 1 hour. After concentration of the reaction solution under reduced pressure, 45 g of nitroiminoimidazolidine and 70 g of 1,3-dimethyl-2-imidazolidinone were added and agitated at 140° to 160° C. for 2 hours. 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, washed with ethyl acetate and dried to give 40.2 g of 1-(3,4-dimethylphenyliminomethyl)-2-nitroiminoimidazolidine.

Workup

  1. customwas placed in a reactor
  2. customequipped with Dean's stark tube
  3. stirringagitated at 140° to 160° C. for 2 hours
  4. additionwas added
  5. filtrationThe resultant crystals were collected by filtration
  6. washwashed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-d3dc8dd5dc08468cafe7513ce07fc15f
Source dataset
uspto-grants-1993_06
Patent number
US05219868

Reaction notes

Loading…