Sodium Hydroxide → 2-(Diphenylmethyleneamino)-3-(4-fluorophenyl)propanenitrile

HRID 390328

反応式

HRID 390328 の反応式
[C:1]1([C:7](=[N:14][CH2:15][C:16]#[N:17])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23]Br)=[CH:21][CH:20]=1.[OH-].[Na+]>C(Cl)Cl.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[C:1]1([C:7](=[N:14][CH:15]([CH2:23][C:22]2[CH:25]=[CH:26][C:19]([F:18])=[CH:20][CH:21]=2)[C:16]#[N:17])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 680214-Fluorobenzyl bromideHCID 612957[(Diphenylmethylene)amino]acetonitrile

生成物 1

HCID 584589102-(Diphenylmethyleneamino)-3-(4-fluorophenyl)propanenitrile収率 92%

試薬・触媒・溶媒 2

HCID 5963Benzyltrimethylammonium chloride触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(diphenylmethyleneamino)acetonitrile (1.21 g, 5.47 mmol, 1.0 equiv) in CH2Cl2 (9.12 mL) was added 4-fluorobenzyl bromide (0.75 mL, 6.02 mmol, 1.1 equiv), benzyltrimethylammonium chloride (0.10 g, 0.547 mmol, 0.1 equiv), and NaOH (0.99 mL of a 10 M aqueous solution, 9.85 mmol, 1.8 equiv). The reaction was stirred vigorously for 18 h, at which time TLC analysis indicated complete consumption of the starting nitrile. The reaction was added to water and extracted with CH2Cl2 (×3). The combined CH2Cl2 extracts were dried (Na2SO4) and concentrated in vacuo. The crude product was purified by silica gel chromatography (5-30% ethyl acetate/hexane) to provide the title compound (1.65 g, 92% yield) as a viscous yellow oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.54-7.65 (m, 2H), 7.38-7.48 (m, 4H), 7.31-7.38 (m, 2H), 7.00-7.09 (m, 2H), 6.89-6.97 (m, 2H), 6.84 (d, J=6.30 Hz, 2H), 4.35 (dd, J=7.81, 6.04 Hz, 1H), 3.10-3.29 (m, 2H); LCMS (ES+, (M+H)+) m/z 329.25.

後処理

  1. customconsumption of the starting nitrile
  2. additionThe reaction was added to water
  3. extractionextracted with CH2Cl2 (×3)
  4. dry with materialThe combined CH2Cl2 extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography (5-30% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-bcd505dce2a9457487636a9990a7264e
出典データセット
uspto-grants-2013_02
特許番号
US08383639B2

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