Ethyl Acetate → 2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-1,3-benzothiazole-6-carboxamide

HRID 70816ノート

反応式

HRID 70816 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][C:32]=1[N:33]=[C:34]1[S:38]S[N:36]=[C:35]1Cl)[C:5]([NH:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:27])([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[CH2:28][CH3:29])=[O:6].C(OCC)(=O)C>N1C=CC=CC=1.[Cu]I>[C:35]([C:34]1[S:38][C:2]2[CH:3]=[C:4]([C:5]([NH:7][C:8]3[C:13]([CH3:14])=[CH:12][C:11]([C:15]([F:27])([C:20]([F:26])([F:25])[C:21]([F:24])([F:23])[F:22])[C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=3[CH2:28][CH3:29])=[O:6])[CH:30]=[CH:31][C:32]=2[N:33]=1)#[N:36]

参加物

5

反応物 2

HCID 8857Ethyl AcetateHCID 866729733-bromo-4-{[4-chloro-5H-1,2,3-dithiazol-5-ylidene]amino}-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]benzamide

生成物 1

HCID 866729752-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-1,3-benzothiazole-6-carboxamide収率 49.6%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1049Pyridine溶媒

実験手順

3-bromo-4-{[4-chloro-5H-1,2,3-dithiazol-5-ylidene]amino}-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]benzamide (0.195 g) and copper(I) iodide (0.057 g) were suspended in pyridine (5 ml), and irradiated(150° C., 20 minutes). After cooling, to the reaction mixture was added ethyl acetate. The mixture was washed with 1N hydrochloric acid and water, and dried over anhydrous magnesium sulfate. The drying agent (anhydrous magnesium sulfate) was removed by filtration and the solvent was distilled off under the reduced pressure. The residue was purified by column chromatography to obtain 2-cyano-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]-1,3-benzothiazole-6-carboxamide (0.076 g, 49%).

後処理

  1. customirradiated(150° C., 20 minutes)
  2. temperatureAfter cooling, to the reaction mixture
  3. washThe mixture was washed with 1N hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  6. distillationthe solvent was distilled off under the reduced pressure
  7. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-c4f0a571843b4dddaee150a7791a0df2
出典データセット
uspto-grants-2014_09
特許番号
US08822691B2

反応ノート

読み込み中…