N1-(4,5-DICHLORO-2-NITROPHENYL)ACETAMIDE

3, 4-Dichloroacetanilide (II) (150 g, 0.74 moles) was slowly added to a reactor containing sulfuric acid (270 g, 99percent, 2.7 moles) at 13 °C, followed by stirring for 0.5 hours and then cooling to 8 °C. To this, oleum (422 g, 31.1percent, 4.61 moles) was added slowly, to obtain a mixture. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3, 4-dichloroacetanilide (II) and the resultant sulfuric acid in the mixture was 1: 10. The mixture was further cooled to 3 °C, and nitric acid (51 g, 98percent, 0.79 moles) was slowly added to the mixture over 5 hours. The resultant mixture was further stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). 3, 4-Dichloroacetanilide was completely consumed within 1 hour and a product mixture was obtained. The product mixture was carefully poured over 1650 g ice in 200 ml water while maintaining the temperature below 15 °C, followed by stirring for 15 min to obtain a dispersion. The dispersion was filtered to obtain a residue comprising 2-nitro-4, 5-dichloroacetanilide (I). The residue was washed with water till it was free of residual acid, and the washed residue was dried to obtain 2-nitro-4, 5-dichloroacetanilide (I) (174 g, yield = 95.23percent, HPLC purity = 97.83percent). (0069) HPLC analysis of the product showed the presence of 1.46percent III.Experiment 3: 3, 4-Dichloroacetanilide (II) (150 g, 0.735 moles), sulfuric acid (156.0 g, 99percent w/w, 1.576 moles), oleum (260.5 g, 31.1percent w/w, 2.844 moles), and nitric acid (51 g, 98percent w/w, 0.79 moles) were used. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3, 4-Dichloroacetanilide (II) to the resultant sulfuric acid in the mixture was 1:6. The reaction conditions, and product yield and purity are summarized in Table 1. (0074) 177 g of 2-nitro-4, 5-dichloroacetanilide (I) was obtained (yield = 92percent and HPLC purity of 92percent). HPLC analysis of product showed the presence of 6percent of III. 3, 4-Dichloroacetanilide (II) (150 g, 0.74 moles) was slowly added to a reactor containing sulfuric acid (270 g, 99percent, 2.7 moles) at 13 °C, followed by stirring for 0.5 hours and then cooling to 8 °C. To this, oleum (422 g, 31.1percent, 4.61 moles) was added slowly, to obtain a mixture. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3, 4-dichloroacetanilide (II) and the resultant sulfuric acid in the mixture was 1: 10. The mixture was further cooled to 3 °C, and nitric acid (51 g, 98percent, 0.79 moles) was slowly added to the mixture over 5 hours. The resultant mixture was further stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). 3, 4-Dichloroacetanilide was completely consumed within 1 hour and a product mixture was obtained. The product mixture was carefully poured over 1650 g ice in 200 ml water while maintaining the temperature below 15 °C, followed by stirring for 15 min to obtain a dispersion. The dispersion was filtered to obtain a residue comprising 2-nitro-4, 5-dichloroacetanilide (I). The residue was washed with water till it was free of residual acid, and the washed residue was dried to obtain 2-nitro-4, 5-dichloroacetanilide (I) (174 g, yield = 95.23percent, HPLC purity = 97.83percent). (0069) HPLC analysis of the product showed the presence of 1.46percent III.3, 4-Dichloroacetanilide (II) (150 g, 0.74 moles) was slowly added to a reactor containing sulfuric acid (270 g, 99percent, 2.7 moles) at 13 °C, followed by stirring for 0.5 hours and then cooling to 8 °C. To this, oleum (422 g, 31.1percent, 4.61 moles) was added slowly, to obtain a mixture. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3, 4-dichloroacetanilide (II) and the resultant sulfuric acid in the mixture was 1: 10. The mixture was further cooled to 3 °C, and nitric acid (51 g, 98percent, 0.79 moles) was slowly added to the mixture over 5 hours. The resultant mixture was further stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). 3, 4-Dichloroacetanilide was completely consumed within 1 hour and a product mixture was obtained. The product mixture was carefully poured over 1650 g ice in 200 ml water while maintaining the temperature below 15 °C, followed by stirring for 15 min to obtain a dispersion. The dispersion was filtered to obtain a residue comprising 2-nitro-4, 5-dichloroacetanilide (I). The residue was washed with water till it was free of residual acid, and the washed residue was dried to obtain 2-nitro-4, 5-dichloroacetanilide (I) (174 g, yield = 95.23percent, HPLC purity = 97.83percent). (0069) HPLC analysis of the product showed the presence of 1.46percent III.Experiment 3: 3, 4-Dichloroacetanilide (II) (150 g, 0.735 moles), sulfuric acid (156.0 g, 99percent w/w, 1.576 moles), oleum (260.5 g, 31.1percent w/w, 2.844 moles), and nitric acid (51 g, 98percent w/w, 0.79 moles) were used. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3, 4-Dichloroacetanilide (II) to the resultant sulfuric acid in the mixture was 1:6. The reaction conditions, and product yield and purity are summarized in Table 1. (0074) 177 g of 2-nitro-4, 5-dichloroacetanilide (I) was obtained (yield = 92percent and HPLC purity of 92percent). HPLC analysis of product showed the presence of 6percent of III. 3, 4-Dichloroacetanilide (II) (150 g, 0.74 moles) was slowly added to a reactor containing sulfuric acid (270 g, 99percent, 2.7 moles) at 13 °C, followed by stirring for 0.5 hours and then cooling to 8 °C. To this, oleum (422 g, 31.1percent, 4.61 moles) was added slowly, to obtain a mixture. The mixture comprised resultant sulfuric acid having strength of 104percent. The molar ratio of 3, 4-dichloroacetanilide (II) and the resultant sulfuric acid in the mixture was 1: 10. The mixture was further cooled to 3 °C, and nitric acid (51 g, 98percent, 0.79 moles) was slowly added to the mixture over 5 hours. The resultant mixture was further stirred and the progress of the reaction was monitored by thin layer chromatography (TLC). 3, 4-Dichloroacetanilide was completely consumed within 1 hour and a product mixture was obtained. The product mixture was carefully poured over 1650 g ice in 200 ml water while maintaining the temperature below 15 °C, followed by stirring for 15 min to obtain a dispersion. The dispersion was filtered to obtain a residue comprising 2-nitro-4, 5-dichloroacetanilide (I). The residue was washed with water till it was free of residual acid, and the washed residue was dried to obtain 2-nitro-4, 5-dichloroacetanilide (I) (174 g, yield = 95.23percent, HPLC purity = 97.83percent). (0069) HPLC analysis of the product showed the presence of 1.46percent III.

Molecular Weight:249.05
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:247.9755474
Monoisotopic Mass:247.9755474
Topological Polar Surface Area:74.9
Heavy Atom Count:15
Complexity:269
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes