Anthranilamide → N-(2-carbamoylphenyl)-2-chloro-6-methoxybenzamide

HRID 2079305

Reaktionsgleichung

Reaktionsgleichung von HRID 2079305
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[Cl:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:13]=1[C:14](Cl)=[O:15]>N1C=CC=CC=1>[C:4]([C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[NH:1][C:14](=[O:15])[C:13]1[C:17]([O:21][CH3:22])=[CH:18][CH:19]=[CH:20][C:12]=1[Cl:11])(=[O:5])[NH2:6]

Komponenten

4

Edukt 2

HCID 6942AnthranilamideHCID 12892677HCID 12892677, Verbindung

Produkt 1

HCID 58010809N-(2-carbamoylphenyl)-2-chloro-6-methoxybenzamideAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

2-Amino-benzamide (6.9 g, 50.8 mmol) was dissolved in 50 mL of pyridine and cooled to 0° C. 2-Chloro-6-methoxy-benzoyl chloride was added dropwise to the solution. After complete addition, the reaction was left to stir at room temperature for three days, which resulted in formation of a brown, cloudy solution. The reaction mixture was then poured into 150 mL of ice water. The precipitate was filtered and washed twice with water, twice with THF and finally twice with CH2Cl2 to obtain N-(2-carbamoylphenyl)-2-chloro-6-methoxybenzamide (13.3 g, 43.7 mmol, 86%).

Aufarbeitung

  1. additionAfter complete addition
  2. waitthe reaction was left
  3. customwhich resulted in formation of a brown, cloudy solution
  4. filtrationThe precipitate was filtered
  5. washwashed twice with water, twice with THF and finally twice with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-f96f3f7a4f8c4759956386e625934998
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928107B2

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