反応 #92501

反応方程式

2-Chloroethylamine hydrochloride

(E)-1-(4-Chloro-3-nitrophenyl)-3-(2-(3-(1-(hydroxyimino)ethyl)phenyl)propan-2-yl)urea

sodium hydride

→

9

収率 46.0%

(E)-1-(2-(3-(1-((2-aminoethoxy)imino)ethyl)phenyl)propan-2-yl)-3-(4 chloro-3-nitrophenyl)urea

収率 46.0%

溶媒

DMF

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe reaction mixture was stirred at room temperature for 2 h
2. 2
   その他the volatiles were removed under reduced pressure
3. 3
   workup.DISSOLUTIONThe residue was dissolved in a minimal amount of methanol
4. 4
   その他purified by column chromatography

実験手順

(E)-1-(4-Chloro-3-nitrophenyl)-3-(2-(3-(1-(hydroxyimino)ethyl)phenyl)propan-2-yl)urea (7b, 100 mg, 0.25 mmol) in 3 mL dry DMF was added drop wise at 0° C. to sodium hydride dispersion in mineral oil (15.3 mg, 0.50 mmol). The resulting mixture was stirred at 0° C. for 30 min. 2-Chloroethylamine hydrochloride (29.6 mg, 0.25 mmol) in 2 mL DMF was added and the reaction mixture was stirred at room temperature for 2 h and then the volatiles were removed under reduced pressure. The residue was dissolved in a minimal amount of methanol and purified by column chromatography using methanol/chloroform to obtained 9 (49 mg, 46%) 1H NMR (DMSO-d6, 400 MHz) δ 1.61 (s, 6H), 2.19 (s, 3H), 2.79 (t, J=5.6 Hz, 2H), 4.05 (t, J=5.6 Hz, 2H), 6.95 (s, 1H), 7.34 (t, J=7.6 Hz, 1H), 7.42-7.47 (m, 3H), 7.56 (d, J=8.8 Hz, 1H), 7.65 (s, 1H), 8.20 (d, J=2 Hz, 1H), 9 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) δ 13.3, 30.1, 41.6, 55.4, 76.6, 113.8, 116.2, 122.7, 122.9, 124.5, 126.3, 128.8, 132.2, 136.5, 141.1, 148.1, 148.8, 154.2, 154.9; ESI-HRMS for C20H24Cl N5O4 (M+H)+ calcd. 434.1595. found. 434.1595.

出典