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CAS No. :2150-93-8 MDL No. :MFCD00018148
Formula : C8H7Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :SCYGGCAQZFJGRF-UHFFFAOYSA-N
M.W : 204.05 Pubchem ID :16530
Synonyms :

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Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2150-93-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 2150-93-8 ]
  • Downstream synthetic route of [ 2150-93-8 ]

[ 2150-93-8 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 2150-93-8 ]
  • [ 6641-64-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792
  • 2
  • [ 2150-93-8 ]
  • [ 5462-30-6 ]
YieldReaction ConditionsOperation in experiment
95.23% at 3 - 13℃; for 6.5 h; 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.
Reference: [1] Patent: WO2018/91978, 2018, A1, . Location in patent: Page/Page column 7-8
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 10, p. 1786 - 1792
  • 3
  • [ 2150-93-8 ]
  • [ 5462-30-6 ]
YieldReaction ConditionsOperation in experiment
92% at 3 - 13℃; for 6.5 h; 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.
Reference: [1] Patent: WO2018/91978, 2018, A1, . Location in patent: Page/Page column 7-8; 9
  • 4
  • [ 625-58-1 ]
  • [ 2150-93-8 ]
  • [ 5462-30-6 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 31,34, 35
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