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

HRID 339526

Reaktionsgleichung

Reaktionsgleichung von HRID 339526
[F:1][C:2]([F:15])([F:14])[CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][CH:6]=1.S(Cl)(Cl)=O.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][C:29]3[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:30]=3[N:31]=2)=[CH:23][CH:22]=1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[F:14][C:2]([F:1])([F:15])[CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([C:27]3[S:28][C:29]4[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:30]=4[N:31]=3)=[CH:25][CH:26]=2)=[O:11])=[CH:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 37639014-(2,2,2-Trifluoroethoxy)benzoic acid

Produkt 1

HCID 673118514-(2,2,2-Trifluoroethoxy)-N-[4-(6-methoxybenzothiazol-2-yl)-phenyl]-benzamideAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 4-(2,2,2-trifluoroethoxy)benzoic acid (0.30 g, 1.35 mmol) and thionyl chloride (0.32 g, 2.72 mmol) in chloroform (5 ml) was heated under reflux for 4 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 (0.34 g, 1.35 mmol) in dry pyridine (15 ml) to give the title compound (0.56 g, 91%) as a pale yellow solid after work-up.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 4 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-d6518cb0a1b843b49c336e9e89e2d4b3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

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