Hydrochloric Acid → 5-(4-Cyano-2-phenoxyphenyl)hydantoin

HRID 343935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 343935
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)#[N:2].[C-]#N.[K+].[C:21](=[O:24])([O-])[O-].[NH4+:25].[NH4+:26].Cl.[CH2:28]([OH:30])C.O>O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]2[NH:26][C:28](=[O:30])[NH:25][C:21]2=[O:24])=[C:5]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1)#[N:2]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 19096565Water ethanolHCID 219054244-Cyano-2-phenoxybenzaldehyde

Produkt 1

HCID 700771845-(4-Cyano-2-phenoxyphenyl)hydantoin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A stirred mixture of 4-cyano-2-phenoxybenzaldeyde (2.23 g, 10 mmol), potassium cyanide (1.30 g, 20 mmol) and ammonium carbonate (3.84 g, 40 mmol) in ethanol-water (30 ml, 1:1) was heated to 80° C. for 2 hours in a sealed vessel. The mixture was diluted with water (30 ml), cautiously acidified to pH1 with 5M hydrochloric acid (20 ml) and extracted with ethyl acetate (30 ml). The extracts were washed with water (30 ml), dried, filtered and evaporated to a viscous brown oil (3.1 g). Chromatography on flash silica (graded elution with 2 to 4% methanol in dichloromethane) gave 5-(4-cyano-2-phenoxyphenyl)hydantoin as a yellow foam.

Aufarbeitung

  1. extractionextracted with ethyl acetate (30 ml)
  2. washThe extracts were washed with water (30 ml)
  3. customdried
  4. filtrationfiltered
  5. customevaporated to a viscous brown oil (3.1 g)

Quellen und Nachweise

ORD-Eintrag
ord-a8d3db47a04a4cb486bfe1bf6134c96a
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05863947

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