p-Anisoyl chloride → HCID 10591644, Verbindung

HRID 264027

Reaktionsgleichung

Reaktionsgleichung von HRID 264027
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:22](Cl)(=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>ClCCl>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([NH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:31])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 68297N-Phenyl-o-phenylenediamine

Produkt 1

HCID 10591644HCID 10591644, VerbindungAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A vigorously stirring solution of N-phenyl-1,2-phenylenediamine (20.15 g) in dichloromethane (325 ml) and triethylamine (11.07 g) was cooled in an ice/acetone bath under nitrogen. p-Anisoyl chloride (18.66 g) dissolved in dichloromethane (100 ml) was added dropwise over a 20 minute period while maintaining a temperature of <5° C. The reaction mixture was allowed to warm to ambient temperature and stirred for two hours. The organic solution was washed successively with water (200 ml), 2N aqueous HCl (80 ml), and saturated brine solution (160 ml), then dried over sodium sulfate and passed through a pad of silica (150 g). The silica was eluted with ethyl acetate (1 L) and the eluent was evaporated in vacuo to a pink solid. The solid was triturated overnight with ethyl ether (350 ml), cooled in an ice bath, filtered, and dried in vacuo to give the title compound as a light pink solid (21.67 g). 1H (300 MHz, CDCl3): d 3.82 (s, 3H), 5.75 (br s, 1H), 6.80-6.91(m, 5H), 7.12-7.29 (m, 5H), 7.62 (d, J=8.8 Hz, 2H), 8.15 (dd, J=1.7, 7.8 Hz, 1H), 8.36 (s, 1H); TLC (EtOAc/Hex, 1:4): Rf =0.24; m.p.: 148°-150° C.

Aufarbeitung

  1. additionwas added dropwise over a 20 minute period
  2. temperaturewhile maintaining a temperature of <5° C
  3. washThe organic solution was washed successively with water (200 ml), 2N aqueous HCl (80 ml), and saturated brine solution (160 ml)
  4. dry with materialdried over sodium sulfate
  5. washThe silica was eluted with ethyl acetate (1 L)
  6. customthe eluent was evaporated in vacuo to a pink solid
  7. customThe solid was triturated overnight with ethyl ether (350 ml)
  8. temperaturecooled in an ice bath
  9. filtrationfiltered
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2f37e187e9c9439e86f918932f20cd67
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646140

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