Hydrochloric Acid → 5-(2-Hydroxy-ethyl)-3-(4-methyl-benzyl)-imidazolidine-2,4-dione

HRID 1985215

Reaktionsgleichung

Reaktionsgleichung von HRID 1985215
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][NH:7][C:8]([NH:10][CH:11]2[CH2:15][CH2:14][O:13][C:12]2=[O:16])=[O:9])=[CH:4][CH:3]=1.C[O-].[Na+].C(Cl)Cl.Cl>CO>[OH:13][CH2:14][CH2:15][CH:11]1[NH:10][C:8](=[O:9])[N:7]([CH2:6][C:5]2[CH:17]=[CH:18][C:2]([CH3:1])=[CH:3][CH:4]=2)[C:12]1=[O:16]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 10942334Sodium MethoxideHCID 577189951-(4-Methyl-benzyl)-3-(2-oxo-tetrahydro-furan-3-yl)-urea

Produkt 1

HCID 577189415-(2-Hydroxy-ethyl)-3-(4-methyl-benzyl)-imidazolidine-2,4-dioneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of crude 1-(4-methyl-benzyl)-3-(2-oxo-tetrahydro-furan-3-yl)-urea (48.5 g, assume 0.137 mol) in MeOH (1.5 L) was treated with sodium methoxide (21.1 g, 0.391 mol) and heated to reflux under N2 for 2 h until done by thin layer chromatography (9:1 CH2Cl2:MeOH). The reaction was cooled and the solvent removed in vacuo to give a residue that was combined with aqueous 1 N HCl (640 mL) and extracted with EtOAc. The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford 24.72 g (73%) of crude 5-(2-hydroxy-ethyl)-3-(4-methyl-benzyl)-imidazolidine-2,4-dione as a yellow solid which was carried on in the next step without purification. MS (ES+) Calc'd for C13H17N2O3 (M+1) 249. Found m/z 249 (100%). 1H NMR.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux under N2 for 2 h
  3. temperatureThe reaction was cooled
  4. customthe solvent removed in vacuo
  5. customto give a residue that
  6. extractionextracted with EtOAc
  7. dry with materialThe organic layer was dried (MgSO4)
  8. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-65cf6274f4924a1c81316903fbdba7c8
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544812B2

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