Ammonia → HCID 12952928, compound

HRID 2286208Notes

Reaction equation

HRID 2286208 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][CH2:7][CH2:8][CH:9]1[CH2:13][N:12]([CH2:14][CH3:15])[C:11](=O)[N:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[NH3:23]>>[ClH:3].[Cl:6][CH2:7][CH2:8][CH:9]1[CH2:13][N:12]([CH2:14][CH3:15])[C:11](=[NH:23])[N:10]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 222Ammonia2×HCID 24813Phosphorus oxychlorideHCID 12952926HCID 12952926, compound

Product 1

HCID 12952928HCID 12952928, compound

Procedure

To 250 ml of phosphorus oxychloride was added 95.6 g (0.378 mole) of 4-(2-chloroethyl-1-ethyl-2-oxo-3-phenyl imidazolidine and the mixture stirred at 70°-100° C. for 3.5 hours and concentrated on the rotary evaporator, yielding an oil. The oil was added to approximately 500 ml of liquid ammonia and stirred while the ammonia was allowed to evaporate. The residue was partitioned between chloroform and dilute NaOH. The chloroform layer was concentrated and the residue dissolved in isopropyl ether. The isopropyl ether was treated with carbon black and filtered. The ether was made acidic with ethereal HCl and the resulting precipitate was collected by decanting the ether. The residue was crystallized from isopropoyl alcohol and isopropyl ether. Yield 61 g (56%); m.p. 175°-177° C. Analytical sample recrystallization from isopropyl alcohol and isopropyl ether; m.p. 176°-177.5° C.

Workup

  1. concentrationconcentrated on the rotary evaporator
  2. customyielding an oil
  3. customto evaporate
  4. customThe residue was partitioned between chloroform and dilute NaOH
  5. concentrationThe chloroform layer was concentrated
  6. dissolutionthe residue dissolved in isopropyl ether
  7. additionThe isopropyl ether was treated with carbon black
  8. filtrationfiltered
  9. customthe resulting precipitate was collected
  10. customby decanting the ether
  11. customThe residue was crystallized from isopropoyl alcohol and isopropyl ether
  12. customAnalytical sample recrystallization from isopropyl alcohol and isopropyl ether

Sources & evidence

ORD record
ord-370c44eba4754f54915d7d738cef7a14
Source dataset
uspto-grants-1982_04
Patent number
US04327098

Reaction notes

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