Sulfuric Acid → HCID 136403420, compound

HRID 258121Notes

Reaction equation

HRID 258121 reaction equation
[CH:1]([O-:5])([O-])[O:2][CH3:3].[CH3:6]N1CCN(C)C1=O.S(=O)(=O)(O)O.[N+:19]([N:22]=[C:23]1[NH:27][CH2:26][CH2:25][NH:24]1)([O-:21])=[O:20]>>[CH3:6][O:5][CH:1]([O:2][CH3:3])[N:24]1[CH2:25][CH2:26][NH:27][C:23]1=[N:22][N+:19]([O-:21])=[O:20]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 53629101MethylorthoformateHCID 135413413N-nitroimidazolidin-2-imine

Product 1

HCID 136403420HCID 136403420, compound

Procedure

22.0 g of methyl orthoformate was dropped in about 2 hours in a mixture of 10 g of 2-nitroiminoimidazolidine, 20 ml of 1,3-dimethyl-2-imidazolidinone and 0.05 g of sulfuric acid at 150° C., followed by heating under reflux for further 1 hour while removing the resultant distillate by means of the Dean-Stark trap. After cooling to room temperature, the mixture was poured into water, and extracted with ethyl acetate. After washing with water, the extract was dried with anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure. The resultant crude crystals were sludged with ether to give 1.9 g of 1-dimethoxymethyl-2-nitroiminoimidazolidine.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for further 1 hour
  3. customwhile removing the resultant distillate by means of the Dean-Stark trap
  4. additionthe mixture was poured into water
  5. extractionextracted with ethyl acetate
  6. washAfter washing with water
  7. dry with materialthe extract was dried with anhydrous magnesium sulfate
  8. distillationafter which the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d5bd9db9d5e041e1b57b4581b836d1b2
Source dataset
uspto-grants-1993_11
Patent number
US05264584

Reaction notes

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