N-(4-bromo-2-nitrophenyl)acetamide → N-Acetyl 4-(3-furanyl)-2-nitroaniline

HRID 581950

Reaktionsgleichung

Reaktionsgleichung von HRID 581950
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2].[O:15]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16]1.C(=O)(O)[O-].[Na+]>O.C(COC)OC.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:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:17]2[CH:18]=[CH:19][O:15][CH:16]=2)=[CH:7][C:6]=1[N+:12]([O-:14])=[O:13])(=[O:3])[CH3:2]

Komponenten

7

Edukt 3

HCID 136690N-(4-bromo-2-nitrophenyl)acetamideHCID 516892Sodium BicarbonateHCID 2734358Furan-3-boronic acid

Produkt 1

HCID 54094756N-Acetyl 4-(3-furanyl)-2-nitroanilineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1d from Example 18 (8.5 g, 32.8 mmol), 3-furanylboronic acid (3.67 g, 32.8 mmol), sodium bicarbonate (13.8 g, 0.16 mol) and tetrakis(triphenylphosphine)palladium(0) (0.5 g) in a mixture of water (40 ml) and dimethoxyethane (80 ml) is heated to 80° C. under a stream of nitrogen over night. After cooling the mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate and concentrated under reduced pressure.(*). The residue is dissolved in 40 ml dimethoxyethane. Aqueous sodium hydroxide (78 ml, 1 M) is added and the mixture is stirred at ambient temperature over night. The mixture is poured into water and rendered acidic with diluted hydrochloric acid. The precipitate is filtered off, washed with water and dried to yield 1e (5.09 g, 76%). Mp 152-154° C.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue is dissolved in 40 ml dimethoxyethane
  7. additionAqueous sodium hydroxide (78 ml, 1 M) is added
  8. additionThe mixture is poured into water
  9. filtrationThe precipitate is filtered off
  10. washwashed with water
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3e5b9130d7dd4c5483cca17b90d6c1eb
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922724

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