Propyl chloroformate → (4-Bromo-2,6-dimethyl-phenyl)-carbamic acid propyl ester

HRID 1820141

Reaktionsgleichung

Reaktionsgleichung von HRID 1820141
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5]([NH2:6])=[C:4]([CH3:10])[CH:3]=1.Cl[C:12]([O:14][CH2:15][CH2:16][CH3:17])=[O:13].O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:15]([O:14][C:12](=[O:13])[NH:6][C:5]1[C:7]([CH3:9])=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[CH3:10])[CH2:16][CH3:17]

Komponenten

6

Edukt 4

HCID 7998Propyl chloroformateHCID 8028TetrahydrofuranHCID 11430Potassium Carbonate2×HCID 905494-Bromo-2,6-xylidine

Produkt 1

HCID 11572790(4-Bromo-2,6-dimethyl-phenyl)-carbamic acid propyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

4-Bromo-2,6-dimethyl-aniline (4.3 g) and propyl chloroformate (2.70 mL) were mixed in acetonitrile (50 mL) and tetrahydrofuran (20 mL) and the reaction mixture was heated to reflux for 1 hour. Potassium carbonate (4.5 g) was added and the reaction mixture was refluxed for 1 hour and then poured onto crushed ice and saturated aqueous potassium carbonate (50 mL). The product was collected by filtration and washed with water (100 mL) to furnish 5.26 g (86% yield) of the title compound as a solid. LC-MS (m/z) 287 (MH+); tR=3.18, (UV, ELSD) 99%, 95%. 1H NMR (500 MHz, CDCl3): 0.93 (t, 3H), 1.62 (m, 2H), 2.15 (s, 6H), 4.00 (t, 2H), 7.28 (s, 2H), 8.74 (b, 1H).

Aufarbeitung

  1. temperatureto reflux for 1 hour
  2. temperaturethe reaction mixture was refluxed for 1 hour
  3. additionpoured
  4. filtrationThe product was collected by filtration
  5. washwashed with water (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-b1ab29ad37a54c84b1e5f7b25c4b48a7
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07601870B2

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