Thionyl Chloride → 2-[[4-(4-Pyridyl)benzoyl]amino]-N-(4-methoxyphenyl)benzamide Hydrochloride

HRID 395841

Reaktionsgleichung

Reaktionsgleichung von HRID 395841
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O.[NH2:20][C:21]1[CH:37]=[CH:36][CH:35]=[CH:34][C:22]=1[C:23]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)=[O:24]>C1(C)C=CC=CC=1.N1C=CC=CC=1>[ClH:18].[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:20][C:21]3[CH:37]=[CH:36][CH:35]=[CH:34][C:22]=3[C:23]([NH:25][C:26]3[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=3)=[O:24])=[O:13])=[CH:14][CH:15]=2)=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 24386Thionyl ChlorideHCID 4788202-amino-N-(4-methoxyphenyl)benzamideHCID 15208114-(Pyridin-4-yl)benzoic acid

Produkt 1

HCID 181744352-[[4-(4-Pyridyl)benzoyl]amino]-N-(4-methoxyphenyl)benzamide HydrochlorideAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a stirring suspension of 4-(4-pyridyl)benzoic acid (0.2 g, 1 mmol) in toluene (35 mL) was added thionyl chloride (0.55 mL, 7.5 mmol) and the mixture was heated to reflux. After 1 h the solution was cooled and added to a solution of 2-amino-N-(4-methoxyphenyl)benzamide (0.176 g, 0.73 mmol) in pyridine (2 mL) and toluene (5 mL). After stirring for 48 h, the solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was separated and washed with sat. NaHCO3, brine and dried (MgSO4), filtered and concentrated to give 103 mg of brown solid which was chromatographed by RPHPLC Method B. Upon standing, a sample of the title compound (14 mg, 4%) crystalized from one of the product containing fractions.

Aufarbeitung

  1. temperaturethe mixture was heated to reflux
  2. temperatureAfter 1 h the solution was cooled
  3. customthe solvent was removed in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. customThe organic phase was separated
  6. washwashed with sat. NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f64df43c3e664dbc9dab3e6aa122d8da
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605626B2

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