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

HRID 979894Notes

Reaction equation

HRID 979894 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].[H-].[Na+].[CH3:18]I.O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][N:12]([CH3:18])[C:11]2=[O:15])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 3186721-(4-nitrophenyl)imidazolidin-2-one

Product 1

HCID 137323581-Methyl-3-(4-nitrophenyl)imidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(p-nitrophenyl)-2-imidazolidinone (25 g) in 450 ml of dimethylformamide is stirred under nitrogen and sodium hydride (50%, 6.4 g) added in small portions. The mixture is stirred at 50° for 11/2 hours, cooled to room temperature, and then methyl iodide (25 g) is added. After stirring 2 hours, the pH of the reaction mixture is 9. Another batch of methyl iodide (4 g) is added over 6 hours until the pH of the mixture is about 8. Water (150 ml) is added, the precipitated solid is filtered off, washed with dimethylformamide/water (1:1), then with water (2×150 ml). The solid is dried to give 1-(p-nitrophenyl)-3-methyl-2-imidazolidinone, m.p. 207°-208°.

Workup

  1. stirringAfter stirring 2 hours
  2. filtrationthe precipitated solid is filtered off
  3. washwashed with dimethylformamide/water (1:1)
  4. customThe solid is dried

Sources & evidence

ORD record
ord-a5cf380efde84965aa47145340c469c2
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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