Cyanogen Bromide → 4-Methyl-4-phenyl-4,5-dihydro-oxazol-2-ylamine

HRID 1911500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1911500
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].C([O-])([O-])=O.[K+].[K+].[N:18]#[C:19]Br>C1COCC1>[CH3:5][C:2]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:3][O:4][C:19]([NH2:18])=[N:1]1

Komponenten

5

Edukt 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 3497332-Amino-2-phenylpropan-1-ol

Produkt 1

HCID 593238034-Methyl-4-phenyl-4,5-dihydro-oxazol-2-ylamineAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred, cooled (0° C.) mixture of 2-amino-2-phenyl-propan-1-ol (266 mg) and K2CO3 (292 mg) in THF (5 ml) under an argon atmosphere was added a solution of cyanogen bromide (292 mg) in THF (5 ml). The ice bath was removed and stirring at r.t. was continued for 18 h. The mixture (white suspension) was taken up in EtOAc/H2O 1:1. The aqueous phase was back extracted with EtOAc. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give 4-methyl-4-phenyl-4,5-dihydro-oxazol-2-ylamine (204 mg) as white solid. MS (ISP): 177.1 ([M+H]+)

Aufarbeitung

  1. temperatureTo a stirred, cooled
  2. customThe ice bath was removed
  3. extractionThe aqueous phase was back extracted with EtOAc
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-74eb45af6f134007bc567d86f57f454e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604061B2

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