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Triethylamine → N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]-2,3,5-trichlorobenzamide

HRID 1598112
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1598112
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH2:20][C:21]1[CH:43]=[CH:42][C:24]([C:25]([N:27]2[CH2:33][C:32]3[CH:34]=[CH:35][CH:36]=[CH:37][C:31]=3[CH2:30][C:29]3[CH:38]=[CH:39][CH:40]=[CH:41][C:28]2=3)=[O:26])=[CH:23][CH:22]=1>C(Cl)Cl>[CH:38]1[C:29]2[CH2:30][C:31]3[CH:37]=[CH:36][CH:35]=[CH:34][C:32]=3[CH2:33][N:27]([C:25]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][C:4](=[O:5])[C:3]4[CH:7]=[C:8]([Cl:12])[CH:9]=[C:10]([Cl:11])[C:2]=4[Cl:1])=[CH:43][CH:42]=3)=[O:26])[C:28]=2[CH:41]=[CH:40][CH:39]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 130111162,3,5-Trichlorobenzoyl chlorideHCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Produkt 1

HCID 67624157N-[4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)-carbonyl]phenyl]-2,3,5-trichlorobenzamideAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel
2×

Versuchsvorschrift

A mixture of 366 mg of 2,3,5-trichlorobenzoyl chloride and 151 mg of triethylamine in 2 ml of methylene chloride is stirred while 314 mg of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine in 5 ml of methylene chloride is added. Stirring is continued for 1.5 hours. The reaction mixture is partitioned with water and the organic layer is washed with 1N HCl, water, 0.5N NaOH and brine. The organic layer is dried with Na2 SO4 and passed through a pad of hydrous magnesium silicate. Hexane is added to the filtrate at the boil to give 0.52 g of white solid residue which is purified by column chromatography on silica gel by elution with 2:1 hexane-ethyl acetate to give 120 mg of the desired product as a crystalline solid, m.p. 225°-230° C.

Aufarbeitung

  1. additionis added
  2. customThe reaction mixture is partitioned with water
  3. washthe organic layer is washed with 1N HCl, water, 0.5N NaOH and brine
  4. customThe organic layer is dried with Na2 SO4
  5. additionHexane is added to the filtrate at the boil

Quellen und Nachweise

ORD-Eintrag
ord-5b40d27c852b4b99a8bbc181d71343a2
Quelldatensatz
uspto-grants-1998_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05736538

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