Urea → 1,5-Dimethyl-4-phenylimidazolidin-2-one

HRID 902461

Reaction equation

HRID 902461 reaction equation
[CH3:1][C@H:2](NC)[C@H:3](O)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1.S(=O)(=O)([O-])N.[NH4+].[NH2:19][C:20]([NH2:22])=[O:21].[CH3:23]N1C(=O)CCC1>O>[CH3:23][N:19]1[CH:2]([CH3:1])[CH:3]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:22][C:20]1=[O:21]

Participants

6

Reactant 4

HCID 1176UreaHCID 9294EphedrineHCID 13387N-methyl-2-pyrrolidoneHCID 24482Ammonium sulfamate

Product 1

HCID 2305471,5-Dimethyl-4-phenylimidazolidin-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
177.5 °C

Procedure

1 mol of an ephedrine, 1.025 mol of ammonium sulfamate, 3 mol of urea and the proton-donating compound were introduced into 200 ml of NMP. The reaction mixture was heated to 175 to 180° C. and stirred at this temperature for 2.5 h. It was then cooled to 130° C. and, at this temperature, water was added dropwise to the reaction mixture. Two phases formed. The lower phase was removed at 95° C. The upper phase was further cooled initially to 65° C. Crystals formed at this temperature. It was cooled further to 10° C. and stirred at this temperature for 1 h. The crystals were filtered off with suction and washed twice with cold water. The solid was dried in vacuo at RT overnight.

Workup

  1. additionwas added dropwise to the reaction mixture
  2. customTwo phases formed
  3. customThe lower phase was removed at 95° C
  4. temperatureThe upper phase was further cooled initially to 65° C
  5. customCrystals formed at this temperature
  6. temperatureIt was cooled further to 10° C.
  7. stirringstirred at this temperature for 1 h
  8. filtrationThe crystals were filtered off with suction
  9. washwashed twice with cold water
  10. customThe solid was dried in vacuo at RT overnight

Sources & evidence

ORD record
ord-0c674f87262c463884a0803402d2a8e9
Source dataset
uspto-grants-2008_04
Patent number
US07365210B2

Linked notes

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