Cyclohexanecarbonyl chloride → 4-(2-Chlorophenyl)-9-cyclohexyl-2-ethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine

HRID 963037

Reaktionsgleichung

Reaktionsgleichung von HRID 963037
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[C:18]([CH2:20][CH3:21])[S:17][C:10]=2[N:11]=[C:12]([NH:15][NH2:16])[CH2:13][N:14]=1.[CH:22]1([C:28](Cl)=O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:19]=[C:18]([CH2:20][CH3:21])[S:17][C:10]=2[N:11]2[C:28]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:16][N:15]=[C:12]2[CH2:13][N:14]=1

Komponenten

6

Edukt 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 124342995-(2-Chlorophenyl)-7-ethyl-2-hydrazinyl-3H-thieno[2,3-e]-1,4-diazepine

Produkt 1

HCID 189176634-(2-Chlorophenyl)-9-cyclohexyl-2-ethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepineAusbeute 58,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

5-(2-Chlorophenyl)-7-ethyl-2-hydrazino-3H-thieno[2,3-e] [1,4]diazepine (20 g) was suspended in chloroform (200 ml) at room temperature. Cyclohexanecarboxylic acid chloride (10.1 g) was added, and the mixture was stirred for 3 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated to give an oil. The oil was dissolved in a mixed solvent of toluene (200 ml) and acetic acid (5.4 ml), and the mixture was refluxed for 3 hours. The reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and dried over magnesium sulfate. The solvent was evaporated. The residue was purified by silica gel column chromatography (eluted with ethyl acetate), and isopropyl ether was added to give 15 g of 4-(2-chlorophenyl)-9-cyclohexyl-2-ethyl-6H-thieno[3,2-f] [1,2,4]triazolo[4,3-a] [1,4]diazepine.

Aufarbeitung

  1. washThe reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customto give an oil
  5. temperaturethe mixture was refluxed for 3 hours
  6. washThe reaction mixture was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated
  9. customThe residue was purified by silica gel column chromatography (eluted with ethyl acetate), and isopropyl ether
  10. additionwas added

Quellen und Nachweise

ORD-Eintrag
ord-62be24d7b7424df099f58b6f3682c35c
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05760032

Verknüpfte Notizen

Wird geladen…