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 70815노트

반응식

HRID 70815 반응식
[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]

참가 물질

6

반응물 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

생성물 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]benzamide수율 85.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a2f1fad240474bd384ddf24297185be5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822691B2

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