反応 #51886

反応方程式

3,4,5-trifluorobenzonitrile

diethanolamine

→

3,5-difluoro-4-[bis(2-hydroxyethyl)amino]benzonitrile

溶媒

N,N-dimethylacetamide

反応条件

後処理

1. 1
   その他The solvent was then evaporated
2. 2
   その他the residue partitioned between CH2Cl2 (200 ml) and H2O (200 ml)
3. 3
   乾燥the organic layer dried (MgSO4)
4. 4
   その他evaporated to dryness
5. 5
   その他The residue was chromatographed
6. 6
   その他to give
7. 7
   その他after recrystallization from toluene, 2.7 g (35%) of pure white crystals

実験手順

A solution of 3,4,5-trifluorobenzonitrile (5 g, 32 mmol) and diethanolamine (6 ml, 85 mmol) in N,N-dimethylacetamide was stirred for 10 days. The solvent was then evaporated, the residue partitioned between CH2Cl2 (200 ml) and H2O (200 ml), the organic layer dried (MgSO4) and evaporated to dryness. The residue was chromatographed using CH2Cl2-EtOAc as eluent to give, after recrystallization from toluene, 2.7 g (35%) of pure white crystals: mp 63-65° C.; 1H NMR δ3.33 (t, 4H, NCH2, J=6 Hz), 3.48 (t, 4H, OCH2, J=6 Hz), 4.43 (bs, 2H, OH), 7.57 (dd, 2H, H2+6, JH2, F3 and H6, F5=8.5 Hz, JH2, F5 and H6, F3=2Hz=22 Hz); 19F NMR δ −116.0 (d, 2F, F3+5, JF3, H2 and F5, 6=7.5 Hz); MS m/z 265 (M+Na+, 10), 243 (M+H+, 100), 211 (M-CH2OH, 85). Anal. (C11H12N2O2F2) C,H,N.

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