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 70816노트

반응식

HRID 70816 반응식
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]

참가 물질

5

반응물 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

생성물 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-carboxamide수율 49.6%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1049Pyridine용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-c4f0a571843b4dddaee150a7791a0df2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822691B2

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