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

HRID 1576837

Reaction equation

HRID 1576837 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-12b6665c574c4cdba7d9f873b7be165b
Source dataset
uspto-grants-1976_09
Patent number
US03983135

Linked notes

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