Hydrogen Peroxide → Ethyl 4-(aminocarbonyl)-3-(cyclopentylamino)benzoate

HRID 906144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 906144
[C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[NH:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)#[N:2].C(=O)([O-])[O-:21].[K+].[K+].OO.O>CS(C)=O>[NH2:2][C:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][C:4]=1[NH:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:21]

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 67404316Ethyl 4-cyano-3-(cyclopentylamino)benzoate

Produkt 1

HCID 67402438Ethyl 4-(aminocarbonyl)-3-(cyclopentylamino)benzoateAusbeute 334,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-cyano-3-(cyclopentylamino)benzoate (363 mg, 1.41 mmol), potassium carbonate (50 mg, 0.36 mmol), and 30% aqueous hydrogen peroxide (0.25 mL) in DMSO (1.5 mL) was stirred at 60° C. for 1 h. After cooling to room temperature, water was added and the resulting mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with water (10 mL) and brine (10 mL), dried over sodium sulfate, filtered and concentrated to give ethyl 4-(aminocarbonyl)-3-(cyclopentylamino)benzoate (333 mg, 86% yield). MS (EI) for C15H20N2O3: 277 (MH+).

Aufarbeitung

  1. extractionthe resulting mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with water (10 mL) and brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e7dfdf5d499a4003a770fd88f7018e26
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012956B2

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