(4-Nitrophenyl)acetic acid → N-Methoxy-N-methyl-2-(4-nitrophenyl)acetamide

HRID 856801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856801
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[CH3:15][NH:16][O:17][CH3:18].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C1C=CN=CC=1)C.O.C(N(CC)CC)C>[CH3:18][O:17][N:16]([CH3:15])[C:11](=[O:13])[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Komponenten

9

Edukt 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 22938759N-Methoxy-N-methyl-2-(4-nitrophenyl)acetamideAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a solution of (4-nitrophenyl)acetic acid (30.0 g), N,O-dimethylhydroxylamine hydrochloride (21.0 g) and 1-hydroxybenzotriazole monohydrate (33.0 g) in DMF (450 ml) were added triethylamine (30 ml) and 4-(N,N-dimethylamino)pyridine (130 mg), and then 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (41.4 g) was added to the mixture, and then, the mixture was stirred overnight under nitrogen atmosphere. Water was added to the mixture, and the mixture extracted with ethyl acetate twice. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate once, with water twice, and with saturated brine once, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained solid was washed with hexane to give N-methoxy-N-methyl-2-(4-nitrophenyl)acetoamide (32.6 g) as colorless crystals.

Aufarbeitung

  1. extractionthe mixture extracted with ethyl acetate twice
  2. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate once
  3. dry with materialwith water twice, and with saturated brine once, and dried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe obtained solid was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-e34154576cea4cbfa2b4fa88fbcbdb9b
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262185B2

Notizen zur Reaktion

Wird geladen…