Hydrochloric Acid → 1-(Phenyl(tetrahydrofuran-2-yl)methyl)urea

HRID 590785Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 590785
Cl.[C:2]1([CH:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[NH2:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-:15][C:16]#[N:17].[K+].Cl.C([O-])(O)=O.[Na+]>O.CCOC(C)=O>[C:2]1([CH:8]([CH:10]2[CH2:14][CH2:13][CH2:12][O:11]2)[NH:9][C:16]([NH2:17])=[O:15])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11378442Potassium cyanateHCID 45791440Oxolan-2-yl(phenyl)methanamine hydrochloride

Produkt 1

HCID 1182717571-(Phenyl(tetrahydrofuran-2-yl)methyl)urea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Phenyl(tetrahydrofuran-2-yl)methanamine HCl (640 mg, 2.99 mmol) was taken up in water (3 ml). Potassium cyanate (1215 mg, 14.97 mmol) and HCl (3 ml, 36.5 mmol) were then added. The reaction mixture was allowed to stir under microwave irradition at 80° C. for 1 hr. Saturated NaHCO3 and EtOAc were added. The products were extracted into EtOAc (3×). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give 1-(phenyl(tetrahydrofuran-2-yl)methyl)urea. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 7.23 (m, 4H), 7.18 (m, 1H), 6.43 (d, J=9.5, 1H), 5.57 (br s, 2H), 4.68-4.47 (dd, J=3.5, J=5.5, 1H), 3.97 (m, 1H), 3.76 (q, J=8.0 1H), 3.56 (q, J=7.0, 1H), 1.79-1.75 (m, 3H), 1.73 (m, 1H).

Aufarbeitung

  1. extractionThe products were extracted into EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4b6d42c2c4434203a208462c36ff9777
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09233979B2

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