Hydrochloric Acid → 1-(5-Chloro-2-methoxyphenyl)-5-phenyl-2,4-imidazolidinedione

HRID 650043

Reaktionsgleichung

Reaktionsgleichung von HRID 650043
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([NH:8][C:9]([NH2:11])=[O:10])[CH:7]=1.O.[C:15]1([C:21]([CH:23]=[O:24])=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.[K+].[Br-]>C(O)C.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([N:8]2[CH:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:23](=[O:24])[NH:11][C:9]2=[O:10])[CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 253877Potassium BromideHCID 347398(5-Chloro-2-methoxyphenyl)ureaHCID 12215922Glyoxal, phenyl-, hydrate

Produkt 1

HCID 158387761-(5-Chloro-2-methoxyphenyl)-5-phenyl-2,4-imidazolidinedione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittel

Versuchsvorschrift

N-(5-Chloro-2-methoxyphenyl)urea (1 g, 5 mmol) and phenylglyoxal monohydrate (760 mg, 5 mmol) were taken up in absolute ethanol (100 ml) and acetic acid (1 ml) and 1 ml of conc. HCl added. The reaction mixture was heated at reflux 3.5 h and allowed to stand at 24° C. for 18 h prior to concentration by rotary evaporation. The residue was dissolved in ethyl acetate, washed with sat'd NaHCO3 solution and brine. Recrystallization from methylene chloride/hexanes gave 1 g (63%) mp 200° C.; IR(KBr, υ=cm−1) 3168, 3064, 1772, 1701, 1504, 1444, 1426, 1408, 1260, 1190, 1150; 1H NMR (300 MHz, CDCl3) δ 3.59 (3H, s), 5.60 (1H, s), 6.80 (1H, d, J=8.8 Hz), 7.14-7.37 (7H, m), 8.92 (1H, br.s); MS(DCl)m/z: 317(MH+); Anal. calcd. for C16H13ClN2O3: C, 60.67; H, 4.13; N, 8.84. Found: C,60.47; H, 4.12; N, 8.80.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux 3.5 h
  3. concentrationto concentration
  4. customby rotary evaporation
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with sat'd NaHCO3 solution and brine
  7. customRecrystallization from methylene chloride/hexanes
  8. customgave 1 g (63%) mp 200° C.

Quellen und Nachweise

ORD-Eintrag
ord-2cfd5841ce4c49db8c9bdc3d7337bb4a
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271249B1

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