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Dimethylformamide → 6-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide

HRID 70803
ノート
印刷プレビュー

反応式

HRID 70803 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:31])([C:27]([F:30])([F:29])[F:28])[C:23]([F:26])([F:25])[F:24])=[CH:17][C:16]=1[CH2:32][CH3:33])=[O:13])[CH:6]=[CH:5]2.[CH3:34][N:35](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:34]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH:14][C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([F:31])([C:23]([F:26])([F:25])[F:24])[C:27]([F:30])([F:28])[F:29])=[CH:17][C:16]=1[CH2:32][CH3:33])=[O:13])[CH:6]=[CH:5]2)#[N:35]
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 2

HCID 6228DimethylformamideHCID 866729626-Bromo-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide

生成物 1

HCID 866729616-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide収率 9%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 11979704
Tetrakis(triphenylphosphine)palladium
触媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

6-Bromo-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide (0.49 g) was dissolved in N,N-dimethylformamide (4 ml), and deaeration was carried out three times under argon atmosphere (i.e., the reaction solution was de-pressurized to 20 mmHg and brought back to atmospheric pressure under argon atmosphere). Zinc cyanide (0.07 g) and tetrakis (triphenylphosphine) palladium(0) (0.11 g) were added thereto and stirred with heating at 80° C. for 7 hours under argon atmosphere. After cooling to room temperature, the reaction solution was diluted with ethyl acetate, and washed with water and saturated brine. The organic phase was 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 silica gel chromatography to obtain 6-cyano-N-[2-ethyl-4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-6-methylphenyl]-2-naphthamide (0.04 g, yield 9%).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and saturated brine
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. customThe drying agent (anhydrous magnesium sulfate) was removed by filtration
  5. distillationthe solvent was distilled off under the reduced pressure
  6. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-5ec451366f62494f9c118ec98fe33e9b
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822691B2

反応ノート

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