반응 #589218

반응 방정식

Oxalyl chloride

3-nitro-4-methylbenzoic acid

→

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

용매

methylene chloride

반응 조건

후처리

1. 1
   기타The 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
   세척The mixture was washed with a saturated aqueous sodium bicarbonate solution
6. 6
   건조dried over magnesium sulphate
7. 7
   기타evaporated The residue
8. 8
   기타was purified by column chromatography
9. 9
   workup.ADDITIONa 250:8:1 mixture of methylene chloride, methanol

실험 절차

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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