Methanol → 3-[(3-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester

HRID 1524263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1524263
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](O)=[O:22])[CH:14]=1.P(Cl)(Cl)(Cl)=O.CO>N1C=CC=CC=1.O>[CH3:10][O:11][C:12](=[O:24])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:20][C:21](=[O:22])[NH:1][C:2]2[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[CH:3]=2)[CH:14]=1

Komponenten

7

Edukt 4

HCID 887MethanolHCID 167023-AminobenzonitrileHCID 24813Phosphorus oxychlorideHCID 13816150[3-(Methoxycarbonyl)phenoxy]acetic acid

Produkt 1

HCID 81732703-[(3-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl esterAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

Cool a solution of 3-aminobenzonitrile (0.35 g, 2.96 mmol) in pyridine (6 mL), to 0° C., and add 3-carboxymethoxy-benzoic acid methyl ester (0.75 g, 3.57 mmol) followed by phosphorous oxychloride (0.34 mL, 3.6 mmol). Warm the mixture to room temperature and stir for 15 hours. Dilute the mixture with water causing a material to oil out of solution. Add MeOH and stir the mixture vigorously causing a solid to slowly form. Collect the solid by filtration, wash with water and dry on the filter pad to provide 0.940 g of 3-[(3-cyano-phenylcarbamoyl)-methoxy]-benzoic acid methyl ester.

Aufarbeitung

  1. customto slowly form
  2. customCollect the solid
  3. filtrationby filtration
  4. washwash with water
  5. customdry on the filter pad

Quellen und Nachweise

ORD-Eintrag
ord-40a8e0df70f446bbbfc3bc380c447f77
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09079880B2

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