N-Phenyl-p-phenylenediamine → N-[2-(4-nitrophenyl)-ethyl]-N'-[4-(phenylamino)phenyl]-urea

HRID 456857

Reaktionsgleichung

Reaktionsgleichung von HRID 456857
ClC(Cl)(O[C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[CH:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.C(N(C(C)C)CC)(C)C.Cl.[N+:37]([C:40]1[CH:48]=[CH:47][C:43]([CH2:44][CH2:45][NH2:46])=[CH:42][CH:41]=1)([O-:39])=[O:38]>ClCCl.O>[N+:37]([C:40]1[CH:41]=[CH:42][C:43]([CH2:44][CH2:45][NH:46][C:5]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:16]3[CH:15]=[CH:14][CH:13]=[CH:18][CH:17]=3)=[CH:21][CH:22]=2)=[O:11])=[CH:47][CH:48]=1)([O-:39])=[O:38]

Komponenten

7

Edukt 4

HCID 7564N-Phenyl-p-phenylenediamineHCID 81531Diisopropylethylamine2×HCID 94429TriphosgeneHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)

Produkt 1

HCID 22646376N-[2-(4-nitrophenyl)-ethyl]-N'-[4-(phenylamino)phenyl]-ureaAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel4×

Versuchsvorschrift

0.5 g (1.7 mmol) of triphosgene is dissolved in 8 ml of dichloromethane in a 100 ml flask, under argon. Using a motorized syringe, a solution of 0.92 g (5 mmol) of 4-aminodiphenylamine and 1.44 ml (8.2 mmol) of diisopropylethylamine in 15 ml of dichloromethane is added over one hour. Five minutes after the addition is finished, 1.01 g (5 mmol) of 4-nitrophenethylamine hydrochloride followed by a solution of 1.44 ml (8.2 mmol) of diisopropylethylamine in 10 ml of dichloromethane are added in a single portion. After agitation for two hours at 20° C., the reaction mixture is diluted with 50 ml of dichloromethane and 20 ml of water. The organic phase is decanted and rewashed with 20 ml of water. After drying over, MgSO4 and filtration, the organic solution is partially concentrated under vacuum. The precipitate formed is collected by filtration and rinsed with dichloromethane. A yellow solid is obtained with a yield of 40%. Melting point: 204–205° C.

Aufarbeitung

  1. additionFive minutes after the addition
  2. additionare added in a single portion
  3. customThe organic phase is decanted
  4. customAfter drying over,
  5. filtrationMgSO4 and filtration
  6. concentrationthe organic solution is partially concentrated under vacuum
  7. customThe precipitate formed
  8. filtrationis collected by filtration
  9. washrinsed with dichloromethane
  10. customA yellow solid is obtained with a yield of 40%

Quellen und Nachweise

ORD-Eintrag
ord-241df8e502d2419685b72757de2dc2fb
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186752B2

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