Hydrochloric Acid → HCID 12876121, compound

HRID 847813Notes

Reaction equation

HRID 847813 reaction equation
ClCCl.[CH3:4][N:5]([CH2:10][CH2:11][CH3:12])[C:6]([NH:8][CH3:9])=[O:7].[C:13]1([N:19]=[C:20]=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C(Cl)(Cl)Cl>[CH3:4][N:5]([CH2:10][CH2:11][CH3:12])[C:6]([N:8]([CH3:9])[C:20]([NH:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 7672Phenyl isocyanateHCID 20567889HCID 20567889, compound

Product 1

HCID 12876121HCID 12876121, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Into 300 ml of anhydrous dichloromethane, 13.0 g (0.1 mol) of 1,3-dimethyl-1-propylurea and 12.0 g (0.1 mol) of phenylisocyanate were added and dissolved. The mixture was ice-cooled under stirring and 26.0 g (0.1 mol) of stannic chloride was added drop-wise. The reaction was then continued at a room temperature for 15 hours and the precipitate formed was separated by filtration. The precipitate thus obtained was added into a mixture of 60 ml of 20% hydrochloric acid/120 ml of chloroform and the stirring was continued until the mixture became transparent. Then the chloroform layer was separated and was washed with water and the chloroform layer was dried with anhydrous sodium sulfate. The chloroform was removed by distillation under reduced pressure and the residue thus obtained was recrystallized from ligroin to obtain 18.6 g (yield: 75%) of 1,3-dimethyl-1-propyl-5-phenylbiuret having a melting point of 63° to 64° C.

Workup

  1. dissolutiondissolved
  2. temperaturecooled
  3. customthe precipitate formed
  4. customwas separated by filtration
  5. customThe precipitate thus obtained
  6. customThen the chloroform layer was separated
  7. washwas washed with water
  8. dry with materialthe chloroform layer was dried with anhydrous sodium sulfate
  9. customThe chloroform was removed by distillation under reduced pressure
  10. customthe residue thus obtained
  11. customwas recrystallized from ligroin

Sources & evidence

ORD record
ord-fe053f5bdafe40a7b4807a79593869d1
Source dataset
uspto-grants-1981_10
Patent number
US04293713

Reaction notes

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