1-(2-Chloroethyl)imidazolidin-2-one → HCID 86685710, compound

HRID 1055271Notes

Reaction equation

HRID 1055271 reaction equation
[Na].[OH:2][C:3]1[C:4]([CH3:13])=[C:5]([C:8]([CH3:12])=[CH:9][C:10]=1[CH3:11])[CH:6]=[O:7].Cl[CH2:15][CH2:16][N:17]1[CH2:21][CH2:20][NH:19][C:18]1=[O:22]>CO.C1(C)C=CC=CC=1>[CH3:13][C:4]1[C:3]([O:2][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][NH:19][C:18]2=[O:22])=[C:10]([CH3:11])[CH:9]=[C:8]([CH3:12])[C:5]=1[CH:6]=[O:7]

Participants

6

Reactant 3

HCID 754351-(2-Chloroethyl)imidazolidin-2-oneHCID 5360545SodiumHCID 148706283-Hydroxy-2,4,6-trimethylbenzaldehyde

Product 1

HCID 86685710HCID 86685710, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of sodium (1.63 g, 0.071 mol) in methanol (60 mL) is added dropwise 3-hydroxy-2,4,6-trimethylbenzaldehyde (11.90 g, 0.073 mol) in anhydrous toluene (300 mL). The mixture is heated under reflux and then the methanol is distilled off (volume of azeotropic mixture collected 80-90 mL). After returning to 80-90° C., (2-chloroethyl)imidazolidin-2-one (10.45 g, 0.070 mol) is added all at once to the reaction medium. After heating for 7 hours under reflux, the solvents are evaporated under reduced pressure (Tbath 50° C., 25 mbar). Dichloromethane (150 mL) and water (30 mL) are added to the mixture obtained. The organic phase is then washed twice with water (20 mL). After drying over Na2SO4, the dichloromethane is evaporated under reduced pressure (Tbath 35° C., 33 mbar). Petroleum ether (3 times 50 mL) and water (50 mL) are added to the mixture obtained (24 g) and the precipitate obtained is filtered and washed on the filter with water (15 mL) and petroleum ether (twice 15 mL).

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux
  3. distillationthe methanol is distilled off
  4. custom(volume of azeotropic mixture collected 80-90 mL)
  5. customAfter returning to 80-90° C.
  6. temperatureAfter heating for 7 hours
  7. temperatureunder reflux
  8. customthe solvents are evaporated under reduced pressure (Tbath 50° C., 25 mbar)
  9. additionDichloromethane (150 mL) and water (30 mL) are added to the mixture
  10. customobtained
  11. washThe organic phase is then washed twice with water (20 mL)
  12. dry with materialAfter drying over Na2SO4
  13. customthe dichloromethane is evaporated under reduced pressure (Tbath 35° C., 33 mbar)
  14. additionPetroleum ether (3 times 50 mL) and water (50 mL) are added to the mixture
  15. customobtained (24 g)
  16. customthe precipitate obtained
  17. filtrationis filtered
  18. washwashed on the
  19. filtrationfilter with water (15 mL) and petroleum ether (twice 15 mL)

Sources & evidence

ORD record
ord-08b84fbf5a0a469c97b1686acf16cd92
Source dataset
uspto-grants-2016_07
Patent number
US09394380B2

Reaction notes

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