2,4-Difluorophenyl isocyanate → N-[4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)urea

HRID 1657219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657219
[NH2:1][C:2]1[C:3]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])=[C:4]2[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:5]2=[N:6][CH:7]=1.[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[N:28]=[C:29]=[O:30]>O1CCCC1>[Cl:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:3]1[C:2]([NH:1][C:29]([NH:28][C:22]2[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=2[F:20])=[O:30])=[CH:7][N:6]=[C:5]2[S:8][C:9]([CH2:11][CH3:12])=[CH:10][C:4]=12

Komponenten

4

Edukt 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 197871805-Amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine

Produkt 1

HCID 9889640N-[4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)ureaAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine (288 mg) in tetrahydrofuran (3 ml) was added 2,4-difluorophenyl isocyanate (0.13 ml) and the mixture was stirred at room temperature for 18 hours, and then the solvent was distilled off. To the residue was added isopropyl ether to obtain N-[4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridin-5-yl]-N'-(2,4-difluorophenyl)urea as crystals (416 mg, 93.9 %). Colorless prisms were obtained by recrystallization from acetone-hexane, mp: 217°-218° C.

Aufarbeitung

  1. distillationthe solvent was distilled off
  2. additionTo the residue was added isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-b192eb97969f4c4e9ef803e89ab51ffc
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05256782

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