Pyridine → 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

HRID 70815ノート

反応式

HRID 70815 の反応式
[NH2:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[C:14]([CH3:15])=[CH:13][C:12]([C:16]([F:28])([C:21]([F:27])([F:26])[C:22]([F:25])([F:24])[F:23])[C:17]([F:20])([F:19])[F:18])=[CH:11][C:10]=2[CH2:29][CH3:30])=[O:7])=[CH:4][C:3]=1[Br:33].[Cl-].[Cl:35][C:36]1[C:40](Cl)=[S+:39][S:38][N:37]=1.N1C=CC=CC=1>O1CCCC1.ClCCl>[Br:33][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:2]=1[N:1]=[C:40]1[S:39][S:38][N:37]=[C:36]1[Cl:35])[C:6]([NH:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16]([F:28])([C:21]([F:26])([F:27])[C:22]([F:23])([F:24])[F:25])[C:17]([F:19])([F:20])[F:18])=[CH:11][C:10]=1[CH2:29][CH3:30])=[O:7]

参加物

6

反応物 3

HCID 1049PyridineHCID 110958474,5-Dichloro-1,2,3-dithiazol-1-ium chlorideHCID 866729744-amino-3-bromo-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 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収率 85.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-amino-3-bromo-N-[2-ethyl-6-methyl-4-(1,1,1,2,3,3,4,4,4-nonafluorobutan-2-yl)phenyl]benzamide (0.254 g) was dissolved in tetrahydrofuran (20 ml). To the mixture was added 4,5-dichloro-1,2,3-dithiazol-1-ium chloride (0.106 g), and stirred at room temperature for 2 hours. To the reaction mixture was added pyridine (0.091 g) in dichloromethane, and stirred at room temperature for 1 hour. The solvent was removed under reduced pressure. To the residue was added water and extracted twice with ethyl acetate. The organic phases were combined and washed with 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 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 (0.270 g, 85%).

後処理

  1. stirringstirred at room temperature for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. additionTo the residue was added water
  4. extractionextracted twice with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  8. distillationthe solvent was distilled off under the reduced pressure
  9. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-a2f1fad240474bd384ddf24297185be5
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…