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Chemical Structure| 1219741-20-4 Chemical Structure| 1219741-20-4

Structure of 1219741-20-4

Chemical Structure| 1219741-20-4

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Product Details of [ 1219741-20-4 ]

CAS No. :1219741-20-4
Formula : C6H6ClIN2
M.W : 268.48
SMILES Code : NC1=CC(I)=C(Cl)C=C1N
MDL No. :MFCD14706075

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Application In Synthesis of [ 1219741-20-4 ]

* 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.

  • Downstream synthetic route of [ 1219741-20-4 ]

[ 1219741-20-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 335349-57-0 ]
  • [ 1219741-20-4 ]
YieldReaction ConditionsOperation in experiment
74% With ammonium chloride; In ethanol; water; at 70℃; for 2.0h; Next, a solution of <strong>[335349-57-0]5-chloro-4-iodo-2-nitroaniline</strong> (15 g, 50.26 mmol, 1.00 equiv) in ethanol/H2O (400/50 mL), Fe powder (16.9 g, 301.79 mmol, 6.00 equiv) and NH4Cl (8 g, 149.53 mmol, 3.00 equiv) was placed into a 1000-mL round-bottom flask. The resulting solution was stirred for 2 h at 70 C. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 3×500 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×100 mL of brine, dried and concentrated under vacuum. This resulted in 10 g (74%) of 4-chloro-5-iodobenzene-1,2-diamine as a black solid.
Step B 4-chloro-5-iodobenzene-1,2-diamine. To a suspension of <strong>[335349-57-0]5-chloro-4-iodo-2-nitroaniline</strong> (36.5 g, 122 mmol) in EtOH (800 mL) and water (150 mL) was added iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol). The mixture was heated under nitrogen at 50 C. overnight. Additional iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step without further purification.
With water; iron; ammonium chloride; In ethanol; at 60℃; for 40.0h; To a mixture of 5-chloro-4-iodo-2- nitroaniline 1-5 (31.7 g, 106 mmol) and iron powder (59.0 g, 1060 mmol) in 880 mL ethanol was added a solution OfNH4Cl (28 g, 530 mmol) in 240 mL of water. The resulting mixture was mechanically stirred at 60 C for 40 h. After cooling to rt the mixture was filtered and the filtrate reduced to about 500 mL by rotary evaporation. This filtrate was diluted with 1 L of EtOAc and I L of water, and shaken. The organic layer separated, washed with brine, dried (MgSO4) and evaporated to provide crude product. The crude product was dissolved in 80 mL of EtOAc, diluted with 80 mL of hexanes and injected onto a 330 g column Of SiO2, which was pre-eluted with 33% EtOAc in hexanes. The column was subjected to MPLC eluting at 100 mL/min with 33% EtOAc in hexanes (15 min) and then 50% EtOAc (20 min) to provide 5-chloro-4-iodo-l,2- phenylenediamine 1-6. Impure fractions of residue were resubjected to MPLC on a 330 g column of SiO2 by the same method to provide additional 5-chloro-4-iodo-l ,2-phenylenediamme 1-6 as an amorphous solid. 1H NMR (500 MHz, DMSO-d6): delta 4.77 (s, 2H), 4.91 (s, 2H), 6.66 (S5 IH), 6.93 (s5 IH); LC-MS: calculated for C6H6ClIN2 267.9, observed m/e 269.0 (M + H)+.
With iron; ammonium chloride; In ethanol; water; at 50℃;Inert atmosphere; To a suspension of <strong>[335349-57-0]5-chloro-4-iodo-2-nitroaniline</strong> (Intermediate 1, 36.5 g, 122 mmol) in EtOH (800 mL) and water (150 mL) was added iron powder (38 g, 673mmol) and NEta4CI (16 g, 306 mmol). The mixture was heated under nitrogen at 5O0C overnight. Additional iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step without further purification.
With water; iron; ammonium chloride; In ethanol; at 50℃;Inert atmosphere; To a suspension of <strong>[335349-57-0]5-chloro-4-iodo-2-nitroaniline</strong> (Intermediate 6, 36.5 g, 122 mmol) in EtOH (800 niL) and water (150 mL) was added iron powder (38 g, 673mmol) and NH4Cl (16 g, 306 mmol). The mixture was heated under nitrogen at 5O0C overnight. Additional iron powder (38 g, 673 mmol) and NH4Cl (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step without further purification.
With iron; ammonium chloride; In ethanol; water; at 50℃;Inert atmosphere; To a suspension of <strong>[335349-57-0]5-chloro-4-iodo-2-nitroaniline</strong> (36.5 g, 122 mmol) in EtOH (800 mL) and water (150 mL) was added iron powder (38 g, 673 mmol) and NH4C1 (16 g, 306 mmol). The mixture was heated under nitrogen at 50 C overnight. Additional iron powder (38 g, 673 mmol) and NH4C1 (16 g, 306 mmol) were added and heating was continued for 45 h. The reaction mixture was cooled, filtered and concentrated. The resulting residue was re-dissolved in ethyl acetate and washed with sodium bicarbonate solution. The organic phase was concentrated to afford the desired product as a gray solid, which was used in the next step without further purification.

 

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