Benzoyl chloride → N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethylamino)benzamide

HRID 276057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 276057
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17]1([S:23]([NH:26][C:27](=[O:49])[C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[C:30]([NH:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[CH:39][CH:38]=3)[CH:29]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])O.[K+]>CN(C)C=O>[C:17]1([S:23]([NH:26][C:27](=[O:49])[C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:8](=[O:15])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:30]([NH:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[CH:39][CH:38]=3)[CH:29]=2)(=[O:24])=[O:25])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Komponenten

6

Edukt 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516893Potassium BicarbonateHCID 53635937N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide

Produkt 1

HCID 53867694N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethylamino)benzamideAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Triethylamine (0.115 g) and 0.200 g of benzoyl chloride were added to a solution of 0.500 g of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide in 5 ml of N,N-dimethylformamide. The mixture was stirred at room temperature for 15 hours. A potassium hydrogencarbonate aqueous solution was added thereto to stop the reaction. The solvent was distilled off under reduced pressure. The residue was dissolved in a mixture of water and methanol, and the solution was adjusted to a pH of from 5 to 6 with 10% hydrochloric acid. The crystals precipitated were collected, and were dried to obtain 0.393 g of crude N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethyl-amino)benzamide. This crude product was converted to 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-phenyl-benzimidazole [(246), 0.270 g] in the same manner as in Example 183.

Aufarbeitung

  1. customthe reaction
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in a mixture of water and methanol
  4. customThe crystals precipitated
  5. customwere collected
  6. customwere dried

Quellen und Nachweise

ORD-Eintrag
ord-f61e1f252f4c45dca198b4fb434b6c5d
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352985B1

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