2,6-Xylyl isocyanate → N-(1,3-Dimethyl-4-oxoimidazolidin-2-ylidene)-N'-(2,6-dimethylphenyl)urea

HRID 2398583Notes

Reaction equation

HRID 2398583 reaction equation
[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[N:4]([CH3:8])[C:3]1=[NH:9].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[N:18]=[C:19]=[O:20]>O1CCCC1>[CH3:1][N:2]1[CH2:6][C:5](=[O:7])[N:4]([CH3:8])[C:3]1=[N:9][C:19]([NH:18][C:12]1[C:11]([CH3:10])=[CH:16][CH:15]=[CH:14][C:13]=1[CH3:17])=[O:20]

Participants

4

Reactant 2

HCID 987872,6-Xylyl isocyanateHCID 140604272-Imino-1,3-dimethylimidazolidin-4-one

Product 1

HCID 54230876N-(1,3-Dimethyl-4-oxoimidazolidin-2-ylidene)-N'-(2,6-dimethylphenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6.35 g (0.050 mole) of 1,3-dimethyl-2-iminoimidazolidin-4-one and 7.25 g (0.050 mole) of 2,6-dimethylphenylisocyanate in 75 ml. of dry tetrahydrofuran is stirred at room temperature for two hours followed by refluxing it for thirty minutes. The reaction mixture is evaporated in vacuo to give a solid, which is crystallized from tetrahydrofuran-ether. Two more recrystallizations from the same solvent mixture gives pure product, 1-(1,3-dimethyl-4-oxo-2-imidazolidinylidene)-3-(2,6-dimethylphenyl) urea; m.p. 115.5°-118.5° C.

Workup

  1. temperatureby refluxing it for thirty minutes
  2. customThe reaction mixture is evaporated in vacuo
  3. customto give a solid, which
  4. customis crystallized from tetrahydrofuran-ether
  5. customTwo more recrystallizations from the same solvent mixture

Sources & evidence

ORD record
ord-b7ac7b709ef247918f3412a03121a2a4
Source dataset
uspto-grants-1977_05
Patent number
US04025517

Reaction notes

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