N-Phenyl-p-phenylenediamine → N-[4-(phenylamino)phenyl]propanamide

HRID 1957337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957337
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])(O)=O.[Na+].[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>C(Cl)Cl>[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:20](=[O:23])[CH2:21][CH3:22])=[CH:10][CH:9]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 7564N-Phenyl-p-phenylenediamineHCID 62324Propionyl chlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 853805N-[4-(phenylamino)phenyl]propanamideAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A stirred mixture of 1.84 g (10.0 mmol, 1 eq.) of commercial N-phenyl-1,4-phenylenediamine (a black solid) and 1.18 g (14.0 mmol, 1.4 eq.) of NaHCO3 in 40 mL of CH2Cl2 was cooled to 0° C. To this suspension was added a solution of 0.96 mL (11.0 mmol, 1.1 eq.) of propionyl chloride in 10 mL of CH2Cl2 dropwise. The ice bath was removed and the mixture stirred for 1 hour and then poured into a seperatory funnel containing 50 mL of each CH2Cl2 and water. The organic phase was separated and extracted with 50 mL of saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by flash column chromatography (100 g SiO2, 1:1 ethyl acetate-hexanes) to give 1.79 g (75%) of product. 1H NMR (300 MHz, CDCl3) δ7.41 (d, 2H), 7.21-7.43 (m, 2H), 7.14 9 (bs, 1H), 6.96-7.07 (m, 4H) 6.90 (t, 1H), 5.66 (bs, 1H), 2.38 (q, 2H), 1.25 (t, 3H). MS (DCl) m/e 258 (M+NH4)+, 241 (M+H)+.

Aufarbeitung

  1. customThe ice bath was removed
  2. additionpoured into a seperatory funnel
  3. additioncontaining 50 mL of each CH2Cl2 and water
  4. customThe organic phase was separated
  5. extractionextracted with 50 mL of saturated aqueous NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography (100 g SiO2, 1:1 ethyl acetate-hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eb320472994f448cae673f10bda317d3
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05783593

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