N,N-Dimethylaniline → 2-(4-Nitrophenyl)-ethyl [4-(phenylamino)phenyl]-carbamate

HRID 393510

Reaktionsgleichung

Reaktionsgleichung von HRID 393510
Cl[C:2](Cl)([O:4][C:5](=[O:11])OC(Cl)(Cl)Cl)Cl.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([CH:22](O)C)=[CH:18][CH:17]=1)([O-:15])=[O:14].CN(C)C1C=CC=CC=1.[CH:34]1[CH:39]=[CH:38][C:37]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([NH2:47])=[CH:43][CH:42]=2)=[CH:36][CH:35]=1>ClCCl.C(OCC)C.O>[C:37]1([NH:40][C:41]2[CH:46]=[CH:45][C:44]([NH:47][C:5](=[O:11])[O:4][CH2:2][CH2:22][C:19]3[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:21][CH:20]=3)=[CH:43][CH:42]=2)[CH:36]=[CH:35][CH:34]=[CH:39][CH:38]=1

Komponenten

8

Edukt 4

HCID 949N,N-Dimethylaniline2×HCID 7564N-Phenyl-p-phenylenediamineHCID 94429TriphosgeneHCID 5923761-(4-Nitrophenyl)ethan-1-ol

Produkt 1

HCID 121468592-(4-Nitrophenyl)-ethyl [4-(phenylamino)phenyl]-carbamateAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel4×

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

1.18 g (3.9 mmol) of triphosgene is dissolved in 15 ml of dichloromethane in a 250 ml flask, under argon,. Using a motorized syringe, a solution of 2 g (12 mmol) of 4-nitrophenylethanol and 1.7 ml (13 mmol) of N,N-dimethylaniline in 40 ml of dichloromethane is added over 1 hour. The reaction mixture is agitated for a few minutes at 20° C. before adding in one go a solution of 2.2 g (12 mmol) of 4-aminodiphenylamine and 1.7 ml (13 mmol) of N,N-dimethylaniline in 40 ml of dichloromethane. After agitation for one hour at 20° C., the contents of the flask are poured into 100 ml of water. The mixture is diluted with 100 ml of dichloromethane and agitated. The organic phase is decanted, dried over magnesium sulphate, filtered and evaporated under vacuum. The solid obtained is taken up in ethyl ether, triturated and filtered. After drying, a greenish powder is obtained with a yield of 22%. Melting point: 146.4-148° C.

Aufarbeitung

  1. additionbefore adding in one
  2. stirringagitated
  3. customThe organic phase is decanted
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe solid obtained
  8. customtriturated
  9. filtrationfiltered
  10. customAfter drying
  11. customa greenish powder is obtained with a yield of 22%

Quellen und Nachweise

ORD-Eintrag
ord-71b404e4407741cc956e2159a2b2afad
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809090B2

Verknüpfte Notizen

Wird geladen…