Aniline → 2-Amino-6-methyl-N-phenylbenzamide

HRID 221301

Reaktionsgleichung

Reaktionsgleichung von HRID 221301
S(Cl)(Cl)=O.[NH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([OH:10])=O.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1C=CC=CC=1>[NH2:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:7]=1[C:8]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:10]

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 24386Thionyl ChlorideHCID 1512106-Methylanthranilic acid

Produkt 1

HCID 167877862-Amino-6-methyl-N-phenylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Thionyl chloride (14.5 mL, 198 mmol) was added to a solution of 2-amino-6-methylbenzoic acid (10.0 g, 66.1 mmol) in benzene (250 mL). The resulting suspension was heated to reflux and stirred overnight. After cooling, the reaction was concentrated in vacuo, and the resulting residue was dissolved in chloroform (300 mL). Aniline (15 mL, 165 mmol) was added, and the mixture heated to reflux. After three hours, the reaction was allowed to cool and the resulting suspension was filtered. The filtrate was subjected to flash chromatography, and the crude product recrystallized from isopropanol to provide compound 15 as a yellow crystalline solid. MS (ES): m/z 227 (M+H), 134. 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.75 (d, 2H, J=7.9 Hz), 7.32 (t, 2H, J=7.8 Hz), 7.07 (t, 1H, J=7.3 Hz), 7.00 (t, 1H, J=7.8 Hz), 6.58 (d, 1H, J=8.1 Hz), 6.46 (d, 1H, J=7.4 Hz), 4.98 (br. s, 2H), 2.21 (s, 3H). The reaction described above and compound 15 are shown below.

Aufarbeitung

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. concentrationthe reaction was concentrated in vacuo
  5. dissolutionthe resulting residue was dissolved in chloroform (300 mL)
  6. temperaturethe mixture heated to reflux
  7. waitAfter three hours
  8. temperatureto cool
  9. filtrationthe resulting suspension was filtered
  10. customthe crude product recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-dc1b9f2d8f8e492ea813945c0e2fa393
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207153B2

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