Water → HCID 178424814, compound

HRID 2398582Notes

Reaction equation

HRID 2398582 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]([NH2:12])=[N:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:22]=1[N:28]=[C:29]=[O:30].O>CN(C=O)C>[CH3:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH3:20])[C:22]=1[NH:28][C:29]([N:12]=[C:10]1[NH:9][C:8](=[O:13])[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:11]1)=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 987872,6-Xylyl isocyanateHCID 178508942HCID 178508942, compound

Product 1

HCID 178424814HCID 178424814, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A suspension of 6.95 g (0.0306 mole) of 5,5-diphenyl-2-amino-2-imidazoline-4-one in 300 ml of dry DMF is treated with 4.5 g (0.0306 mole) of 2,6-dimethylphenylisocyanate. The reaction mixture is stirred at 40° C. for two hours. It is then poured into cold water and the resulting solids are filtered off. To the crude product is added 30 ml of water with heating; acetone is added to the heated slurry until all solids go in solution (1.5 liters of acetone). The solution is then evaporated to a volume of 300 ml., chilled, and the resulting solids are filtered off to give 1-(2,6-dimethylphenyl)-3-(5,5-diphenyl-4-oxo-2-imidazolidinylidene) urea, the pure product; no m.p. up to 350° C.

Workup

  1. filtrationthe resulting solids are filtered off
  2. additionTo the crude product is added 30 ml of water
  3. temperaturewith heating
  4. additionacetone is added to the heated slurry until all solids
  5. customThe solution is then evaporated to a volume of 300 ml
  6. temperature, chilled
  7. filtrationthe resulting solids are filtered off

Sources & evidence

ORD record
ord-31ef0d2f858641d982e2c1f32a276978
Source dataset
uspto-grants-1977_05
Patent number
US04025517

Reaction notes

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