Water → (5-Chloro-2-nitrophenyl)-(1-(R)-methyl-2,2-dimethylpropyl)amine

HRID 250748

Reaktionsgleichung

Reaktionsgleichung von HRID 250748
[NH2:1][C@@H:2]([C:4]([CH3:7])([CH3:6])[CH3:5])[CH3:3].C(=O)([O-])[O-].[K+].[K+].O.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[C:18](F)[CH:17]=1>C1COCC1>[Cl:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[C:20]([NH:1][C@H:2]([CH3:3])[C:4]([CH3:7])([CH3:6])[CH3:5])[CH:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 5324845(R)-3,3-Dimethyl-2-aminobutane

Produkt 1

HCID 66869060(5-Chloro-2-nitrophenyl)-(1-(R)-methyl-2,2-dimethylpropyl)amineAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

Add 2-(R)-amino-3,3-dimethylbutane (20 mL, 0.148 mol), potassium carbonate (14.3 g, 0.104 mol) and water (50 mL) to a solution of 4-chloro-2-fluoronitrobenzene (13.3 g, 0.076 mol) in THF (450 mL) and stir at 75° C. for 3 h Cool to ambient temperature. Concentrate to ½ volume, dilute with ethyl acetate and wash with 1N HCl (4×100 mL), water, saturated sodium bicarbonate, saturated sodium chloride, dry with magnesium sulfate and concentrate to give the title compound as an orange solid (19.6 g, quant).

Aufarbeitung

  1. temperatureCool to ambient temperature
  2. concentrationConcentrate
  3. additiondilute with ethyl acetate
  4. washwash with 1N HCl (4×100 mL), water, saturated sodium bicarbonate, saturated sodium chloride
  5. dry with materialdry with magnesium sulfate
  6. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-9f13736c3cc0452799f7c738cd081826
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863310B2

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