Methyl Isocyanate → 1-[1-(4-Bromo-phenyl)ethyl]-3-methyl-urea

HRID 858577

Reaktionsgleichung

Reaktionsgleichung von HRID 858577
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][N:12]=[C:13]=[O:14]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:10][C:13]([NH:12][CH3:11])=[O:14])[CH3:9])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 12228Methyl IsocyanateHCID 853000(R)-4-bromo-alpha-methylbenzylamine

Produkt 1

HCID 471273271-[1-(4-Bromo-phenyl)ethyl]-3-methyl-ureaAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a stirred solution of (R)-(+)-1-(4-bromophenyl)ethylamine (0.5 g, 2.49 mmol) in anhydrous CH2Cl2 was added methyl isocyanate (0.15 mL, 2.49 mmol). The resulting solution was stirred at 25° C. overnight. CH2Cl2 was evaporate and residue partitioned between EtOAC and 1 N HCl. The organic layer was washed with H2O, brine and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (80% EtOAc in hexanes) to provide the desired product (0.60 g, 94%) as a white solid.

Aufarbeitung

  1. customCH2Cl2 was evaporate
  2. customresidue partitioned between EtOAC and 1 N HCl
  3. washThe organic layer was washed with H2O, brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash column chromatography (80% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2ab5911dda914485bf2df388fee5d0f1
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148226B2

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