Thionyl Chloride → 4-(4,4,4-Trifluorobutoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamide

HRID 339528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339528
[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][C:31]3[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=3[N:33]=2)=[CH:25][CH:24]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:16][C:2]([F:1])([F:17])[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]3[S:30][C:31]4[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:32]=4[N:33]=3)=[CH:27][CH:28]=2)=[O:13])=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 223614014-(4,4,4-Trifluorobutoxy)benzoic acid

Produkt 1

HCID 673125284-(4,4,4-Trifluorobutoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamideAusbeute 87,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 4-(4,4,4-trifluorobutoxy)benzoic acid (0.20 g, 0.806 mmol) and thionyl chloride (0.42 g, 3.54 mmol) in chloroform (5 ml) was heated under reflux for 8 h. The reaction mixture was cooled to room temperature and the excess reagent and solvent was removed under reduced pressure to give the crude acid chloride. The amide was prepared as described in the Amide Coupling section using the crude acid chloride and 2-(4-aminophenyl)-6-methoxybenzothiazole (0.206 g, 0.806 mmol) in dry pyridine (10 ml) to give the title compound (0.343 g, 87%) as a colourless solid after work-up.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 8 h
  3. customthe excess reagent and solvent was removed under reduced pressure
  4. customto give the crude acid chloride
  5. customThe amide was prepared

Quellen und Nachweise

ORD-Eintrag
ord-d06e25573834415e9dabda2a1e5b6968
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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