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

HRID 339526

反応式

HRID 339526 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d6518cb0a1b843b49c336e9e89e2d4b3
出典データセット
uspto-grants-2014_11
特許番号
US08895313B2

関連ノート

読み込み中…