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Ethyl Acetate → N-[2-chloro-5-pyridyl]-3-(trifluoromethyl)benzamide

HRID 395914
ノート
印刷プレビュー

反応式

HRID 395914 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:8])=[N:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[F:18][C:19]([F:30])([F:29])[C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24].C(OCC)(=O)C>C(#N)C>[Cl:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([C:19]([F:18])([F:29])[F:30])[CH:21]=2)=[CH:7][N:6]=1
参加物反応条件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 8857Ethyl AcetateHCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 793055-Amino-2-chloropyridineHCID 81531Diisopropylethylamine

生成物 1

HCID 9796373N-[2-chloro-5-pyridyl]-3-(trifluoromethyl)benzamide収率 94.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile
溶媒

反応条件

温度
55 °C

実験手順

To a stirring solution of 5-amino-2-chloropyridine (129 mg, 1 mmol) and N,N-diisopropylethylamine (209 μL, 1.2 mmol) in dry acetonitrile (5 mL) was added 3-(trifluoromethyl)benzoyl chloride (151 μL, 1 mmol). The resulting solution was heated at 55° C. for 3 h. After cooling to room temperature ethyl acetate (10 mL) was added and the solution was washed with water (2×10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure and the crude material was purified by column chromatography (4:1, hexane/ethyl acetate) to afford the desired product as a white solid (284 mg, 94%).

後処理

  1. additionwas added
  2. washthe solution was washed with water (2×10 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was removed under reduced pressure
  5. customthe crude material was purified by column chromatography (4:1, hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-4a18751262a1408c9d3935b825e30a61
出典データセット
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06605725B2

反応ノート

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