Dimethylformamide → Acetamide, N-[4-cyano-2-nitro-6-(phenylmethoxy)phenyl]-

HRID 2239287Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2239287
Br[C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH:16][C:17](=[O:19])[CH3:18])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.[CH3:23][N:24](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:23]([C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]([NH:16][C:17](=[O:19])[CH3:18])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1)#[N:24]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 67220372N-(2-(benzyloxy)-4-bromo-6-nitrophenyl)acetamide

Produkt 1

HCID 68576258Acetamide, N-[4-cyano-2-nitro-6-(phenylmethoxy)phenyl]-Ausbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of N-{4-bromo-2-nitro-6-[(phenylmethyl)oxy]phenyl}acetamide (6.5 g, 17.8 mmol, STEP 1), zinc cyanide (4.18 g, 35.6 mmol), and tetrakis(triphenylphosphine)palladium (2.06 g, 1.78 mmol) in N,N-dimethylformamide (100 mL) was heated to 170° C. for 20 minutes in the microwave synthesizer (Biotage, Emrys Optimizer). After cooling to room temperature, the suspension was filtered, and washed with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate, and concentrated in vacuum. The residual solid was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1) to afford the title compound as a white solid (5.5 g, 99%).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. filtrationthe suspension was filtered
  3. washwashed with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuum
  7. customThe residual solid was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9d0b863ace354758aa2c32c4dd3e8132
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723321B2

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