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

HRID 393511

Reaktionsgleichung

Reaktionsgleichung von HRID 393511
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. dry with materialAfter drying over MgSO4 and filtration
  5. concentrationthe organic solution is partially concentrated under vacuum
  6. customThe precipitate formed
  7. filtrationis collected by filtration
  8. washrinsed with dichloromethane
  9. customA yellow solid is obtained with a yield of 40%

Quellen und Nachweise

ORD-Eintrag
ord-eb4af331b3904c088d74bc51c3b1c18a
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809090B2

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