1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(2-Chlorophenyl)-2-ethyl-5-nitrothieno[2,3-b]pyridine

HRID 1657226Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657226
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:33]=[CH:32][CH:31]=[CH:30][C:14]=1[C:15]([C:17]1[CH:21]=[C:20]([CH2:22][CH3:23])[S:19][C:18]=1[NH:24][CH:25]=[CH:26][N+:27]([O-:29])=[O:28])=O>C1C=CC=CC=1>[Cl:12][C:13]1[CH:33]=[CH:32][CH:31]=[CH:30][C:14]=1[C:15]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][N:24]=[C:18]2[S:19][C:20]([CH2:22][CH3:23])=[CH:21][C:17]=12

Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 677573983-(2-Chlorobenzoyl)-2-(2-nitroethenylamino)-5-ethylthiophene

Produkt 1

HCID 197871684-(2-Chlorophenyl)-2-ethyl-5-nitrothieno[2,3-b]pyridineAusbeute 89,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of DBU (5.1 g) in benzene (50 ml) was added dropwise a solution of 3-(2-chlorobenzoyl)-2-(2-nitroethenylamino)-5-ethylthiophene (5.1 g) in dioxanebenzene (1:1, 30 ml) over one hour with stirring under reflux. After refluxing for additional one hour, the mixture was washed with water and dried over MgSO4. The solvent was distilled off and to the residue was added isopropyl ether to obtain 4-(2-chlorophenyl)-2-ethyl-5-nitrothieno[2,3-b]pyridine as crystals (4.3 g, 89.0%). The crystals were recrystallized from isopropyl ether to obtain pale yellow prisms, mp: 72°-73° C.

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureAfter refluxing for additional one hour
  3. washthe mixture was washed with water
  4. dry with materialdried over MgSO4
  5. distillationThe solvent was distilled off and to the residue
  6. additionwas added isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-e467d8e8a43f46cd858969154d73df85
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256782

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