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

HRID 339523ノート

反応式

HRID 339523 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 673117622-methoxy-N-[3-methoxy-4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-5-(trifluoromethoxy)benzamide収率 73.4%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a7c8bcb0be5141e1837200dc4050b4ff
出典データセット
uspto-grants-2014_11
特許番号
US08895313B2

反応ノート

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