Hydrogen Peroxide → 1-(4-Bromophenyl)cyclobutanecarboxamide

HRID 2064439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2064439
OO.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C([O-])([O-])=[O:17].[K+].[K+].O>CS(C)=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:14]([NH2:15])=[O:17])[CH2:13][CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 201116081-(4-Bromophenyl)cyclobutanecarbonitrile

Produkt 1

HCID 471521671-(4-Bromophenyl)cyclobutanecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
27 °C

Versuchsvorschrift

H2O2 (30% 11.3 mL, 118 mmol) was added over 3 h to a stirred mixture of nitrile 1-2c (13.88 g, ˜58.9 mmol) and K2CO3 (1.62 g, 11.8 mol) in 59 mL of DMSO at 40-87° C., cooling with a water bath. The resulting mixture was cooled to 27° C. and water (100 mL) was added over 30 min. Crystalline product 1-3c formed. More water (100 mL) was added over 1 h. The resulting slurry was aged at RT for 16 h before filtration. The cake was rinsed with 100 mL of water and then with 100 mL of heptane. After drying in a vacuum oven at 50° C., product 1-3c was obtained as a white solid.

Aufarbeitung

  1. temperaturecooling with a water bath

Quellen und Nachweise

ORD-Eintrag
ord-e63b4e1e7f0d4e5d839321cd7e3fd664
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288407B2

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