Triethylamine → N-(2-amino-4,5-dichlorophenyl)-2-methoxy-4-cyanobenzamide

HRID 1352652Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1352652
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([NH2:22])=[C:17]([NH2:23])[CH:16]=1.C(N(CC)CC)C>ClCCl>[NH2:23][C:17]1[CH:16]=[C:15]([Cl:14])[C:20]([Cl:21])=[CH:19][C:18]=1[NH:22][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:3]=1[O:2][CH3:1]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 226750494-Cyano-2-methoxybenzoyl chloride

Produkt 1

HCID 21101177N-(2-amino-4,5-dichlorophenyl)-2-methoxy-4-cyanobenzamideAusbeute 86,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 2-methoxy-4-cyanobenzoyl chloride (2 g, 10 mmol) in dichloromethane (20 ml) was added dropwise in 1 h to a solution of 4,5-dichlorophenylendiamine (3.54 g, 20 mmol) and triethylamine (10.1 g=13.9 ml, 100 mmol) in dichloromethane (20 ml). Stirring was continued for additional two hours. The solvent was removed under vacuum and the residue was triturated with water (50 ml), filtered and dried at 50° C. under vacuum. The solid was suspended in diethyl ether (150 ml), stirred for 1 h, filtered and dried under vacuum to give 2.9 g of N-(2-amino-4,5-dichlorophenyl)-2-methoxy-4-cyanobenzamide (yield 43%), mp>250° C.

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated with water (50 ml)
  3. filtrationfiltered
  4. customdried at 50° C. under vacuum
  5. stirringstirred for 1 h
  6. filtrationfiltered
  7. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ded22f44dbe0478798e9caf097d87fec
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220769B2

Notizen zur Reaktion

Wird geladen…