(1R)-(+)-1-(4-Fluorophenyl)ethylamine → (R)-1-(1-(4-fluorophenyl)ethyl)urea

HRID 590774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590774
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[O-:11][C:12]#[N:13].[K+]>Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:12]([NH2:13])=[O:11])[CH3:9])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6950187(1R)-(+)-1-(4-Fluorophenyl)ethylamineHCID 11378442Potassium cyanate

Produkt 1

HCID 117601722(R)-1-(1-(4-fluorophenyl)ethyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

(R)-1-(4-Fluorophenyl)ethanamine (5.15 g, 37.0 mmol) was taken up in HCl (2N, 40 mL) and potassium cyanate (15.01 g, 185 mmol) was added. The mixture was stirred at 80° C. for 3 h. Upon cooling to room temperature, a precipitate formed which was collected by filtration and washed with water. The solid was partitioned between water and EtOAc, and the aqueous phase extracted once more with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to give (R)-1-(1-(4-fluorophenyl)ethyl)urea. MS ESI calc'd. for C9H11FN2O [M+1]+ 183. found 183.

Aufarbeitung

  1. temperatureUpon cooling to room temperature
  2. customa precipitate formed which
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customThe solid was partitioned between water and EtOAc
  6. extractionthe aqueous phase extracted once more with EtOAc
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d36bd88c69534b799ea41fc4267c8c23
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233979B2

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