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Thionyl Chloride → 2-Trifluoromethyl-n-[4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-4-(methoxy)benzamide

HRID 339522
ノート
印刷プレビュー

反応式

HRID 339522 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:4]=1.S(Cl)(Cl)=O.COC1C(C(F)(F)F)=CC(C(Cl)=O)=CC=1.[NH2:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]2[S:43][C:44]3[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[CH:47][C:45]=3[N:46]=2)=[CH:38][CH:37]=1>N1C=CC=CC=1>[F:13][C:12]([F:15])([F:14])[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([NH:35][C:36]1[CH:37]=[CH:38][C:39]([C:42]2[S:43][C:44]3[CH:50]=[C:49]([O:51][CH3:52])[CH:48]=[CH:47][C:45]=3[N:46]=2)=[CH:40][CH:41]=1)=[O:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24386Thionyl ChlorideHCID 3918704-(6-Methoxy-1,3-benzothiazol-2-yl)anilineHCID 27752944-methoxy-2-(trifluoromethyl)benzoic AcidHCID 27752984-Methoxy-3-(trifluoromethyl)benzoyl chloride

生成物 1

HCID 672404602-Trifluoromethyl-n-[4-(6-methoxy-1,3-benzothiazol-2-yl)phenyl]-4-(methoxy)benzamide収率 46%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A stirred mixture of 4-methoxy-2-trifluoromethylbenzoic acid (0.50 g, 2.27 mmol) and thionyl chloride (9 ml) was heated under reflux for 4 h. After cooling to room temperature, the excess reagent was removed under reduced pressure to give crude acid chloride. The amide was prepared as described in the Amide Coupling section using the crude 4-methoxy-5-trifluoromethylbenzoyl chloride and 2-(4-aminophenyl)-6-methoxybenzo thiazole (0.58 g, 2.27 mmol) in dry pyridine (15 ml) to give the title compound (0.478 g, 46%) as pale yellow needles 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 crude acid chloride
  5. customThe amide was prepared

出典と根拠

ORDレコード
ord-d3daccfe68cc4410bdbac4b9d5eab2e2
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08895313B2

反応ノート

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