Hydrochloric Acid → N,N-Dimethyl-2-oxoimidazolidine-1-carboxamide

HRID 1283420Notes

Reaction equation

HRID 1283420 reaction equation
[CH3:1][NH:2][CH3:3].Cl.Cl[C:6]([N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13])=[O:7].[Cl-].[Na+]>O1CCCC1>[CH3:1][N:2]([CH3:3])[C:6]([N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674Dimethylamine2×HCID 5234Sodium ChlorideHCID 832412-Oxoimidazolidine-1-carbonyl chloride

Product 1

HCID 12771220N,N-Dimethyl-2-oxoimidazolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 50 parts by volume of a 50% strength aqueous dimethylamine solution and 70 parts by volume of tetrahydrofurane was adjusted to pH = 8 with 5 N hydrochloric acid. 14.9 parts by weight of N-chlorocarbonyl-imidazolid-2-one were added gradually thereto while stirring and cooling with ice and the pH value was maintained by simultaneous addition of further dimethylamine solution. The mixture was further stirred until the pH was constant, the tetrahydrofurane was then stripped off and the residue was saturated with sodium chloride and repeatedly extracted with ethyl acetate. The organic solution was washed and saturated sodium chloride solution, dried over MgSO4 and filtered, and the solvent was evaporated off. The residue was recrystallized from acetone and dried in a vacuum desiccator over P2O5.

Workup

  1. temperaturecooling with ice
  2. stirringThe mixture was further stirred until the pH
  3. extractionrepeatedly extracted with ethyl acetate
  4. washThe organic solution was washed
  5. dry with materialsaturated sodium chloride solution, dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was evaporated off
  8. customThe residue was recrystallized from acetone
  9. dry with materialdried in a vacuum desiccator over P2O5

Sources & evidence

ORD record
ord-ed8010575e7d48eda6726de83815293e
Source dataset
uspto-grants-1976_08
Patent number
US03975375

Reaction notes

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