Triethylamine → HCID 44212555, Verbindung

HRID 355919

Reaktionsgleichung

Reaktionsgleichung von HRID 355919
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C(N(CC)CC)C.[NH2:17][C:18]1[CH:40]=[CH:39][C:21]([C:22]([N:24]2[CH2:30][C:29]3[CH:31]=[CH:32][CH:33]=[CH:34][C:28]=3[CH2:27][C:26]3[CH:35]=[CH:36][CH:37]=[CH:38][C:25]2=3)=[O:23])=[CH:20][CH:19]=1>C(Cl)Cl>[CH:35]1[C:26]2[CH2:27][C:28]3[CH:34]=[CH:33][CH:32]=[CH:31][C:29]=3[CH2:30][N:24]([C:22]([C:21]3[CH:20]=[CH:19][C:18]([NH:17][C:7]([CH:1]4[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]4)=[O:8])=[CH:40][CH:39]=3)=[O:23])[C:25]=2[CH:38]=[CH:37][CH:36]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 5230583-Cyclohexene-1-carbonyl chlorideHCID 154104675-(4-Aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine

Produkt 1

HCID 44212555HCID 44212555, VerbindungAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 208 mg of 3-cyclohexene-1-carbonyl chloride (prepared from 3-cyclohexene-1-carboxylic acid and thionyl chloride) and 145 mg of triethylamine in 3 ml of methylene chloride is added to a solution of 377 mg of 5-(4-aminobenzoyl)-6,11-dihydro-5H-dibenz[b,e]azepine in 7 ml of methylene chloride. The mixture is stirred for 18 hours, washed with water, 1N HCl, water, 1M NaHCO3 and brine then dried with Na2 SO4. The organic layer is passed through a short column of hydrous magnesium silicate and hexane added to the filtrate at the boil to give 340 mg of the desired product as a crystalline solid, m.p. 234°-236° C.

Aufarbeitung

  1. washwashed with water, 1N HCl, water, 1M NaHCO3 and brine
  2. customthen dried with Na2 SO4
  3. additionadded to the filtrate at the boil

Quellen und Nachweise

ORD-Eintrag
ord-144d35b463604f17845f918d3f2334ea
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834461

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