Dimethyl Sulfoxide → 1-Methyl-3-(4-nitrophenyl)imidazolidin-2-one

HRID 648481Notes

Reaction equation

HRID 648481 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].IC.[OH-].[K+].[CH3:20]S(C)=O>O>[CH3:20][N:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[C:11]1=[O:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodide2×HCID 14797Potassium Hydroxide2×HCID 3186721-(4-nitrophenyl)imidazolidin-2-one

Product 1

HCID 137323581-Methyl-3-(4-nitrophenyl)imidazolidin-2-oneYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21 parts of 1-(4-nitrophenyl)-2-imidazolidinone, 16 parts of iodomethane, 10 parts of potassium hydroxide and 200 parts of dimethyl sulfoxide was stirred for 3 hours at room temperature. Another portion of 16 parts of iodomethane and 10 parts of potassium hydroxide were added. Stirring was continued overnight. 300 Parts of water were added to the reaction mixture and the whole was stirred. The precipitated product was filtered off and crystallized from 4-methyl-2-pentanone, yielding 16.5 parts (74%) of 1-methyl-3-(4-nitrophenyl)-2-imidazolidinone; mp. 214.1°-215.5° C. (7).

Workup

  1. stirringStirring
  2. waitwas continued overnight
  3. stirringthe whole was stirred
  4. filtrationThe precipitated product was filtered off
  5. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-ffc80d2c462c44d5a8bb8de8c0b71fc4
Source dataset
uspto-grants-1988_04
Patent number
US04735942

Reaction notes

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