反応 #589218

反応方程式

Oxalyl chloride

3-nitro-4-methylbenzoic acid

→

N-(3,4-dichlorobenzyl)-4-methyl-3-nitrobenzamide

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他The reaction mixture was evaporated
2. 2
   workup.DISSOLUTIONthe residue was dissolved in methylene chloride (100 ml)
3. 3
   workup.ADDITION3,4-Dichlorobenzylamine (7.04 g), 4-dimethylaminopyridine (0.31 g) and triethylamine (13.9 ml) were added
4. 4
   workup.STIRRINGthe reaction mixture was stirred at ambient temperature for 16 hours
5. 5
   洗浄The mixture was washed with a saturated aqueous sodium bicarbonate solution
6. 6
   乾燥dried over magnesium sulphate
7. 7
   その他evaporated The residue
8. 8
   その他was purified by column chromatography
9. 9
   workup.ADDITIONa 250:8:1 mixture of methylene chloride, methanol

実験手順

Oxalyl chloride (4.8 ml) was added to a solution of 3-nitro-4-methylbenzoic acid (9.06 g) in methylene chloride (100 ml) and DMF (a few drops) and the reaction stirred at ambient temperature for 16 hours. The reaction mixture was evaporated and the residue was dissolved in methylene chloride (100 ml). 3,4-Dichlorobenzylamine (7.04 g), 4-dimethylaminopyridine (0.31 g) and triethylamine (13.9 ml) were added and the reaction mixture was stirred at ambient temperature for 16 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution, dried over magnesium sulphate and evaporated The residue was purified by column chromatography using a 250:8:1 mixture of methylene chloride, methanol and a saturated aqueous ammonium chloride solution as eluent to give N-(3,4-dichlorobenzyl)-4-methyl-3-nitrobenzamide as a solid (9.95 g); NMR Spectrum: (DMSOd6) 2.57 (s, 3H), 4.47 (d, 2H), 7.31 (m, 1H), 7.56 (m, 2H), 7.61 (d, 1H), 8.1 (m, 1H), 8.47 (d, 1H), 9.3 (t, 1H).

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