Triethylamine → N-[4-[(Dibenz[b,f][1,4]thiazepin-10(11H)yl)carbonyl]phenyl]-2-chlorobenzamide

HRID 1456284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1456284
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[NH2:11][C:12]1[CH:34]=[CH:33][C:15]([C:16]([N:18]2[CH2:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[S:21][C:20]3[CH:29]=[CH:30][CH:31]=[CH:32][C:19]2=3)=[O:17])=[CH:14][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[CH:25]1[C:23]2[CH2:24][N:18]([C:16]([C:15]3[CH:14]=[CH:13][C:12]([NH:11][C:4](=[O:5])[C:3]4[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=4[Cl:1])=[CH:34][CH:33]=3)=[O:17])[C:19]3[CH:32]=[CH:31][CH:30]=[CH:29][C:20]=3[S:21][C:22]=2[CH:28]=[CH:27][CH:26]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 691102-Chlorobenzoyl chlorideHCID 5423000210,11-Dihydro-10-(4-aminobenzoyl)dibenz[b,f][1,4]thiazepine

Produkt 1

HCID 67624707N-[4-[(Dibenz[b,f][1,4]thiazepin-10(11H)yl)carbonyl]phenyl]-2-chlorobenzamideAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 385 mg of 2-chloro-benzoyl chloride in 6 ml of methylene chloride at 0° C. is added 0.6 g of 10-(4-aminobenzoyl)-10,11-dihydrodibenz[b,f][1,4]thiazepine followed by 0.375 ml of triethylamine. The reaction mixture is stirred at room temperature for 18 hours. The reaction mixture is washed with 20 ml of water, 1N HCl, 1N Na2CO3, water and dried over MgSO4. The filtrate is evaporated in vacuo to give 0.7 g of yellowish solid which is purified by silica gel chromatography on thick layer plates by elution with 1:1 ethyl acetate-hexane to give 0.3 g of the desired product, m.p. 116°-119° C.

Aufarbeitung

  1. washThe reaction mixture is washed with 20 ml of water, 1N HCl, 1N Na2CO3, water
  2. dry with materialdried over MgSO4
  3. customThe filtrate is evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c2d8f358a79e42bd9c79f6270288b8b5
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05843952

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