Toluene → HCID 58683864, Verbindung

HRID 1692996

Reaktionsgleichung

Reaktionsgleichung von HRID 1692996
[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([O:11][CH3:12])[C:7]=1[C:8]([OH:10])=O.S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[NH2:24][C:25]1[CH:32]=[C:31]([CH3:33])[CH:30]=[CH:29][C:26]=1[C:27]#[N:28]>N1C=CC=CC=1.CN(C=O)C>[C:27]([C:26]1[CH:29]=[CH:30][C:31]([CH3:33])=[CH:32][C:25]=1[NH:24][C:8](=[O:10])[C:7]1[C:6]([O:11][CH3:12])=[CH:5][CH:4]=[CH:3][C:2]=1[F:1])#[N:28]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 27373602-Fluoro-6-methoxybenzoic acidHCID 28012762-Amino-4-methylbenzonitrile

Produkt 1

HCID 58683864HCID 58683864, VerbindungAusbeute 93,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Fluoro-2-anisoic acid (110 g, 0.70 mol) was added in portions over 15 minutes to a mixture of thionyl chloride (230 ml, 3.2 mol), toluene (200 mL), and DMF (1 mL). The resulting mixture was stirred overnight at room temperature. The solution was evaporated to dryness and added dropwise to an ice-bath cooled solution of 2-amino-4-methylbenzonitrile (92.5 g, 0.70 mol) in pyridine (200 mL). The dropping funnel was rinsed with a minimal amount of acetonitrile. The resulting mixture was stirred overnight at room temperature under a nitrogen atmosphere and was subsequently poured into 2 L ice water. The resulting slurry was stirred vigorously for 1 hour. The formed solid was collected by filtration and was washed twice with water. The filter cake was dissolved in 2 L dichloromethane, and this solution was washed with 1 N aq. HCl (400 mL) and with saturated aq. NaCl (400 mL), dried over sodium sulfate, filtered, and evaporated to dryness to give N-(2-cyano-5-methylphenyl)-2-fluoro-6-methoxybenzamide (186 g, 93%) as a brownish solid. 1H-NMR (CDCl3, 200 MHz): δ9.09 (s, 1H), 8.58 (s, 1H), 7.59-7.42 (m, 2H), 7.09-7.02 (m, 1H), 6.94-6.83 (m, 2H), 4.11 (s, 3H), 2.57 (s, 3H) ppm.

Aufarbeitung

  1. customThe solution was evaporated to dryness
  2. additionadded dropwise to an ice-bath
  3. washThe dropping funnel was rinsed with a minimal amount of acetonitrile
  4. stirringThe resulting mixture was stirred overnight at room temperature under a nitrogen atmosphere
  5. additionwas subsequently poured into 2 L ice water
  6. stirringThe resulting slurry was stirred vigorously for 1 hour
  7. filtrationThe formed solid was collected by filtration
  8. washwas washed twice with water
  9. dissolutionThe filter cake was dissolved in 2 L dichloromethane
  10. washthis solution was washed with 1 N aq. HCl (400 mL) and with saturated aq. NaCl (400 mL)
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-79afad60ab7845ab85f341b57c3ff779
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158637B2

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