Triethylamine → HCID 178512293, Verbindung

HRID 1383449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1383449
[C:1]([NH:3][C:4](=[N:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)SC)#[N:2].[CH:14]1[C:24]2[CH2:23][CH2:22][C:21]3[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=3[CH:19]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH2:35])[C:18]=2[CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>N1C=CC=CC=1.C(OCC)C>[CH:25]1[C:21]2[CH2:22][CH2:23][C:24]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:19]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][NH:35][C:4]([NH:3][C:1]#[N:2])=[N:7][C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[C:20]=2[CH:28]=[CH:27][CH:26]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 155219651-Cyano-2-methyl-3-pyridin-4-yl-isothioureaHCID 211877625-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-pentylamine

Produkt 1

HCID 178512293HCID 178512293, VerbindungAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

1-Cyano-2-methyl-3-pyridin-4-yl-isothiourea (573 mg, 3.00 mmol) and 5-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yloxy)-pentylamine (886 mg, 3.00 mmol) were dissolved in pyridine (20 mL). Triethylamine (2 mL, 14 mmol) was added followed by (4-dimethylamino)pyridine (5.0 mg, 0.04 mmol). The reaction mixture was stirred at 86□ C. for 12 hours. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (50 mL). The resulting precipitate was collected by filtration and washed with diethyl ether. The crude product was recrystalized from methanol and diethyl ether to give the desired product as a white crystalline solid (yield 85%). 1H NMR (CDCl3, ppm): 8.54 (dd, 2H), 7.41-7.12 (m, 10H), 5.29 (s, 1H), 3.56-3.41 (m, 4H), 3.32 (dd, 2H), 3.05-2.95 (m, 2H), 1.71-1.41 (m, 6H).

Aufarbeitung

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with diethyl ether
  3. customThe crude product was recrystalized from methanol and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a00b398a02d0438cb7b8d745f9694f8e
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255323B1

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