Thionyl Chloride → 2-methoxy-N-[3-methoxy-4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamide

HRID 339523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 339523
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][C:4]=1[C:5]([OH:7])=O.S(Cl)(Cl)=O.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][C:29]=1[C:30]1[S:31][C:32]2[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:33]=2[N:34]=1)[NH2:26]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][C:4]=1[C:5]([NH:26][C:25]1[CH:27]=[CH:28][C:29]([C:30]2[S:31][C:32]3[CH:38]=[C:37]([O:39][CH3:40])[CH:36]=[CH:35][C:33]=3[N:34]=2)=[C:23]([O:22][CH3:21])[CH:24]=1)=[O:7]

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 27752862-methoxy-5-(trifluoromethoxy)benzoic AcidHCID 672367942-(4-Amino-2-methoxyphenyl)-6-methoxybenzothiazole

Produkt 1

HCID 673117622-methoxy-N-[3-methoxy-4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamideAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A stirred mixture of 2-methoxy-5-trifluoromethoxybenzoic acid (0.248 g, 1.05 mmol) and thionyl chloride (4 ml) was heated under reflux for 4 h. After cooling to room temperature, the excess reagent 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 3-methoxy-4-(6-methoxy-1,3-benzothiazol-2-yl)aniline (0.30 g, 1.05 mmol) in dry pyridine (8 ml) to give the title compound (0.389 g, 73%) as an almost colourless solid after work-up and recrystallisation from acetic acid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a7c8bcb0be5141e1837200dc4050b4ff
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895313B2

Notizen zur Reaktion

Wird geladen…