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

HRID 80685

반응식

HRID 80685 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 584589102-(Diphenylmethyleneamino)-3-(4-fluorophenyl)propanenitrile수율 92%

시약·촉매·용매 2

HCID 5963Benzyltrimethylammonium chloride촉매HCID 6344Dichloromethane용매

실험 절차

(Procedure adapted from J. Org. Chem. 2003, 68, 50-54). 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ea0141a21de0411b964d3477074eb909
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846659B2

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