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[ CAS No. 5326-47-6 ]

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Chemical Structure| 5326-47-6
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CAS No. :5326-47-6 MDL No. :MFCD00007849
Formula : C7H6INO2 Boiling Point : 383.2°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :263.03 g/mol Pubchem ID :72911
Synonyms :

Safety of [ 5326-47-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5326-47-6 ]

  • Upstream synthesis route of [ 5326-47-6 ]
  • Downstream synthetic route of [ 5326-47-6 ]

[ 5326-47-6 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 5326-47-6 ]
  • [ 149-73-5 ]
  • [ 16064-08-7 ]
YieldReaction ConditionsOperation in experiment
94% With ammonium acetate In acetonitrile at 120℃; for 3 h; The procedures of Example I-2 were repeated except that methanol was replaced with acetonitrile. There was obtained 0.98 g (reaction yield: 94percent) of 6-iodoquinazolin-4-one.
93% With ammonium acetate In methanol at 120℃; for 3 h; In a 10-mL volume stainless steel pressure-resistant vessel were placed 1.0 g (3.8 mmol) of 5-iodoanthranilic acid, 0.81 g (7.6 mmol) of methyl orthoformate, 0.59 g (7.6 mmol) of ammonium acetate, and 4.0 mL of methanol. The reaction was carried out at 120°C for 3 hours. After the reaction was complete, the reaction mixture was cooled to room temperature, and 40 mL of water was added to the reaction mixture. The resulting aqueous mixture was stirred for 15 minutes and filtered to give 0.97 g (isolated yield: 93percent) of 6-iodoquinazolin-4-one as a pale gray crystalline product. 6-Iodoquinazolin-4-one had the following characteristics. m.p.: 259°C (decomp.) 1H-NMR (DMSO-d6, δ (ppm)): 7.46 (1H, d, J=8.4Hz), 8.08-8.15 (2H, m), 8.39 (1H, d, J=1.8Hz), 12.5 (1H, brs) CI-MS (m/e): 273 (M+1); [Example I-2] Preparation of 6-iodoquinazolin-4-one The procedures of Example I-1 were repeated except that the amounts of methyl orthoformate and ammonium acetate were changed to 1.61 g (15.2 mmol) and 1.17 g (15.2 mmol), respectively. There was obtained 0.98 g (reaction yield: 94percent) of 6-iodoquinazolin-4-one.
91% at 120℃; for 3 h; The procedures of Example I-2 were repeated except that the amount of methyl orthoformate was changed to 3.60 g (34 mmol) and that no methanol was used. There was obtained 0.94 g (reaction yield: 91percent) of 6-iodoquinazolin-4-one.
90% With ammonium 2,4-dichlorobenzoate In methanol at 120℃; for 3 h; The procedures of Example I-2 were repeated except that ammonium acetate was replaced with 3.20 g (15.2 mmol) of ammonium 2,4-dichlorobenzoate. There was obtained 0.97 g (reaction yield: 90percent) of 6-iodoquinazolin-4-one.
85% With ammonium formate In methanol at 120℃; The procedures of Example I-2 were repeated except that ammonium acetate was replaced with 0.95 g (15.2 mmol) of ammonium formate. After the reaction was complete, the reaction mixture was treated in the manner of Example I-1. There was obtained 0.88 g (isolated yield: 85percent) of 6-iodoquinazolin-4-one as a pale gray crystalline product

Reference: [1] Patent: EP1477481, 2004, A1, . Location in patent: Page 17
[2] Patent: EP1477481, 2004, A1, . Location in patent: Page 16-17
[3] Patent: EP1477481, 2004, A1, . Location in patent: Page 17
[4] Patent: EP1477481, 2004, A1, . Location in patent: Page 17
[5] Patent: EP1477481, 2004, A1, . Location in patent: Page 17
  • 2
  • [ 5326-47-6 ]
  • [ 16064-08-7 ]
YieldReaction ConditionsOperation in experiment
92.6% at 180℃; for 12 h; 2-Amino-5-iodobenzoic acid (II) (6.8 g, 0.05 mol),Mixed with 20ml of formamide and heated to 180°C,Stir the reaction for 12h, cool, pour into ice water, filter,After washing with water, 12.6 g of needle-like crystals of 6-iodoquinazolin-4-one (III) were obtained with a yield of 92.6percent and HPLC purity of 99.83percent.
Reference: [1] Patent: CN105111193, 2018, B, . Location in patent: Paragraph 0017; 0037-0045
[2] Patent: WO2013/116786, 2013, A1,
[3] Patent: WO2014/134169, 2014, A1,
  • 3
  • [ 77287-34-4 ]
  • [ 5326-47-6 ]
  • [ 16064-08-7 ]
YieldReaction ConditionsOperation in experiment
93% at 150℃; for 2 h; Example 5: (Production of 6-iodoquinazolin-4-one); With acetic acid and a base coexisting as a catalyst in the reaction system, 6-iodoquinazolin-4-one was produced in the manner mentioned below. 1.05 g (4 mmol) of 5-iodoanthranilic acid, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.17 g (2.8 mmol) of diethylamine were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150°C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with acetic acid and then dried in vacuum at 70°C for 2 hours to obtain 1.01 g of a crystal. The above mother liquid was 3.98 g. The obtained crystal and the mother liquid were analyzed for the purity by high-performance liquid chromatography using 5-iodo-2-methylbenzoic acid as an internal standard substance; and the purity of the crystal was 99.5 percent, 6-iodoquinazolin-4-one in the mother liquid was a trace, and the yield of 6-iodoquinazolin-4-one was 92.3 percent. The result is shown in Table 2 and Table 3. Examples 6 to 9, and Comparative Examples 3 to 5: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the catalyst was changed. Comparative Examples demonstrate a case with no catalyst, a case with an acid catalyst alone, and a case of a base catalyst alone. The results are shown in Table 2.
93% at 150℃; for 2 h; Example 5: (Production of 6-iodoquinazolin-4-one); With acetic acid and a base coexisting as a catalyst in the reaction system, 6-iodoquinazolin-4-one was produced in the manner mentioned below. 1.05 g (4 mmol) of 5-iodoanthranilic acid, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.17 g (2.8 mmol) of diethylamine were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150°C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with acetic acid and then dried in vacuum at 70°C for 2 hours to obtain 1.01 g of a crystal. The above mother liquid was 3.98 g. The obtained crystal and the mother liquid were analyzed for the purity by high-performance liquid chromatography using 5-iodo-2-methylbenzoic acid as an internal standard substance; and the purity of the crystal was 99.5 percent, 6-iodoquinazolin-4-one in the mother liquid was a trace, and the yield of 6-iodoquinazolin-4-one was 92.3 percent. The result is shown in Table 2 and Table 3. Examples 6 to 9, and Comparative Examples 3 to 5: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the catalyst was changed. Comparative Examples demonstrate a case with no catalyst, a case with an acid catalyst alone, and a case of a base catalyst alone. The results are shown in Table 2.
93% at 120℃; for 4 h; 2-amino-5-iodobenzoic acid (1g, 3.8mmol), formamide (5ml) was heated to 120 °C stirred for 4h. Cooled to room temperature, diluted with 50percent ethanol (10ml). The filter cake were washed with 50percent ethanol (5ml), EtOH/PE (1: 1,10ml), PE (5ml) and dried under vacuum to give a brown solid soil (0.9g, 93percent).
90.1% at 150℃; for 2 h; Example 5: (Production of 6-iodoquinazolin-4-one); With acetic acid and a base coexisting as a catalyst in the reaction system, 6-iodoquinazolin-4-one was produced in the manner mentioned below. 1.05 g (4 mmol) of 5-iodoanthranilic acid, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.17 g (2.8 mmol) of diethylamine were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150°C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with acetic acid and then dried in vacuum at 70°C for 2 hours to obtain 1.01 g of a crystal. The above mother liquid was 3.98 g. The obtained crystal and the mother liquid were analyzed for the purity by high-performance liquid chromatography using 5-iodo-2-methylbenzoic acid as an internal standard substance; and the purity of the crystal was 99.5 percent, 6-iodoquinazolin-4-one in the mother liquid was a trace, and the yield of 6-iodoquinazolin-4-one was 92.3 percent. The result is shown in Table 2 and Table 3. Examples 10 to 12, and Comparative Examples 6 and 7: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the amount of acetic acid or the amount of diethylamine (DEA) relative to 5-iodoanthranilic acid (IAAc) was changed. Comparative Examples demonstrate a case with acetic acid (2.8 mmol) alone and a case with diethylamine (2.8 mmol) alone. The results are shown in Table 3 including Example 5.
90.2% at 150℃; for 2 h; Example 5: (Production of 6-iodoquinazolin-4-one); With acetic acid and a base coexisting as a catalyst in the reaction system, 6-iodoquinazolin-4-one was produced in the manner mentioned below. 1.05 g (4 mmol) of 5-iodoanthranilic acid, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.17 g (2.8 mmol) of diethylamine were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150°C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with acetic acid and then dried in vacuum at 70°C for 2 hours to obtain 1.01 g of a crystal. The above mother liquid was 3.98 g. The obtained crystal and the mother liquid were analyzed for the purity by high-performance liquid chromatography using 5-iodo-2-methylbenzoic acid as an internal standard substance; and the purity of the crystal was 99.5 percent, 6-iodoquinazolin-4-one in the mother liquid was a trace, and the yield of 6-iodoquinazolin-4-one was 92.3 percent. The result is shown in Table 2 and Table 3. Examples 6 to 9, and Comparative Examples 3 to 5: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the catalyst was changed. Comparative Examples demonstrate a case with no catalyst, a case with an acid catalyst alone, and a case of a base catalyst alone. The results are shown in Table 2.
89.9% at 150℃; for 2 h; Example 5: (Production of 6-iodoquinazolin-4-one); With acetic acid and a base coexisting as a catalyst in the reaction system, 6-iodoquinazolin-4-one was produced in the manner mentioned below. 1.05 g (4 mmol) of 5-iodoanthranilic acid, 3.60 g (80 mmol) of formamide, 0.17 g (2.8 mmol) of acetic acid and 0.17 g (2.8 mmol) of diethylamine were put into an autoclave of SUS316 having a capacity of 25 mL and equipped with a stirrer, a thermometer and a pressure gauge in a nitrogen atmosphere, and reacted at 150°C for 2 hours. After the reaction, the reaction liquid was cooled to room temperature, and the precipitated crystal was collected by filtration, washed with acetic acid and then dried in vacuum at 70°C for 2 hours to obtain 1.01 g of a crystal. The above mother liquid was 3.98 g. The obtained crystal and the mother liquid were analyzed for the purity by high-performance liquid chromatography using 5-iodo-2-methylbenzoic acid as an internal standard substance; and the purity of the crystal was 99.5 percent, 6-iodoquinazolin-4-one in the mother liquid was a trace, and the yield of 6-iodoquinazolin-4-one was 92.3 percent. The result is shown in Table 2 and Table 3. Examples 6 to 9, and Comparative Examples 3 to 5: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the catalyst was changed. Comparative Examples demonstrate a case with no catalyst, a case with an acid catalyst alone, and a case of a base catalyst alone. The results are shown in Table 2.
89% at 120℃; for 18 h; Heating / reflux Reflux 2-amino-5-iodo-benzoic acid (Aldrich ; 10 g, 38 mmol) in formamide (30 mL) at 120 °C for 18 h. Upon cooling to room temperature, the product is crystallized from the solvent. The product is collected via filtration and the resulting crystals are washed with ether providing the desired 9.2 g (89percent) of the titled compound as a pale solid. MS ES+ m/e 273.0 (M+1).
86.1% at 150℃; for 2 h; Examples 10 to 12, and Comparative Examples 6 and 7: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the amount of acetic acid or the amount of diethylamine (DEA) relative to 5-iodoanthranilic acid (IAAc) was changed. Comparative Examples demonstrate a case with acetic acid (2.8 mmol) alone and a case with diethylamine (2.8 mmol) alone. The results are shown in Table 3 including Example 5.
85.1% at 150℃; for 2 h; Examples 10 to 12, and Comparative Examples 6 and 7: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the amount of acetic acid or the amount of diethylamine (DEA) relative to 5-iodoanthranilic acid (IAAc) was changed. Comparative Examples demonstrate a case with acetic acid (2.8 mmol) alone and a case with diethylamine (2.8 mmol) alone. The results are shown in Table 3 including Example 5.
82% at 150℃; for 2 h; Examples 6 to 9, and Comparative Examples 3 to 5: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the catalyst was changed. Comparative Examples demonstrate a case with no catalyst, a case with an acid catalyst alone, and a case of a base catalyst alone. The results are shown in Table 2.
81% at 150℃; for 2 h; Examples 6 to 9, and Comparative Examples 3 to 5: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the catalyst was changed. Comparative Examples demonstrate a case with no catalyst, a case with an acid catalyst alone, and a case of a base catalyst alone. The results are shown in Table 2.
81% for 10 h; Reflux Step C: 6-Iodo-4-quinazolinone (compound 1.3) [0104] A solution of 2-amino-5-iodobenzoic acid (14.2 g, 50 mmol) and formamide (100 mL) was refluxed for 10 hours. After cooling to room temperature, water (100 mL) was added. The solid product was collected by filtration, washed with water. Further drying in a vacuum provided 6-Iodo-4-quinazolinone (11 g, 81percent) as a gray solid.
75% at 150℃; for 2 h; Examples 6 to 9, and Comparative Examples 3 to 5: (Production of 6-iodoquinazolin-4-one); The reaction and the post-treatment were carried out in the same manner as in Example 5, for which, however, the catalyst was changed. Comparative Examples demonstrate a case with no catalyst, a case with an acid catalyst alone, and a case of a base catalyst alone. The results are shown in Table 2.
75% at 140℃; General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 °C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2*2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 .x. 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 .x. 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.

Reference: [1] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7
[2] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7
[3] Patent: CN103772371, 2016, B, . Location in patent: Paragraph 0052; 0053
[4] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7; 8
[5] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7
[6] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7
[7] Patent: WO2005/92894, 2005, A1, . Location in patent: Page/Page column 18
[8] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 8
[9] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 8
[10] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7
[11] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7
[12] Patent: WO2011/2523, 2011, A1, . Location in patent: Page/Page column 42-43
[13] Patent: EP1997812, 2008, A1, . Location in patent: Page/Page column 7
[14] European Journal of Medicinal Chemistry, 2012, vol. 50, p. 264 - 273
[15] Journal of the Indian Chemical Society, 1959, vol. 36, p. 787,789, 790
[16] J. Madras Univ., 1954, vol. 24, p. 183,184
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  • [ 3473-63-0 ]
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  • [ 16064-08-7 ]
YieldReaction ConditionsOperation in experiment
81% for 20 h; Heating / reflux A solution of 2-AMINO-5-IODOBENZOIC acid (14.2 g, 50 mmol) and formamidine acetate (6.75 g, 65 mmol) in ethanol (200 ML) was refluxed for 20 hours. After cooling to 0°C the solid product was collected by filtration. Further drying in a vacuum provided 6-IODO-4-QUINAZOLINONE (11 G, 81percent) as a gray solid.
Reference: [1] Patent: WO2004/46101, 2004, A2, . Location in patent: Page 19
[2] Patent: WO2004/43940, 2004, A1, . Location in patent: Page 80
  • 5
  • [ 64392-62-7 ]
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Reference: [1] Journal of Organic Chemistry, 1986, vol. 51, # 5, p. 616 - 620
  • 6
  • [ 68-12-2 ]
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Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 10, p. 3820 - 3832
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  • [ 98556-31-1 ]
Reference: [1] Journal of the Indian Chemical Society, 1959, vol. 36, p. 787,789, 790
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 24, p. 8546 - 8555
[3] Patent: WO2013/116786, 2013, A1,
[4] Patent: WO2014/134169, 2014, A1,
[5] Organic Process Research and Development, 2007, vol. 11, # 3, p. 406 - 413
[6] Organic Process Research and Development, 2005, vol. 9, # 4, p. 440 - 450
[7] Patent: CN103772411, 2016, B,
[8] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 27 - 37
[9] Patent: CN103772371, 2016, B,
[10] Chinese Chemical Letters, 2017, vol. 28, # 6, p. 1220 - 1227
[11] Patent: CN106317026, 2017, A,
[12] Patent: WO2004/43940, 2004, A1,
  • 8
  • [ 118-92-3 ]
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YieldReaction ConditionsOperation in experiment
94% for 3.33333 h; Inert atmosphere; Schlenk technique; Cooling with ice; Darkness Hydrogen peroxide (17 g, 0.17 mol, 35percentaq) was added dropwise over 20 min to an ice-cooled solution of anthranilic acid (20 g, 0.15mol) and ammonium iodide (21 g 0.15 mol) in acetic acid (100 mL) in an open beaker, resulting in a dark colored solution. After 3 h of vigorous stirring at room temperature, a tan precipitate formed. The precipitate was collected in a fritted glass funnel, and washed thoroughly with water until the filtrate was colorless to yield 36 g (94percent) of 5-iodo-2-aminobenzoic acid as a tan colored powder, mp 220-224°C (Lit. 219-221 °C). 1H NMR (300 MHz; DMSO-d6; Figure S4a): 6.64 (d, 1 aromatic H para to CO2, 3J = 9 Hz), 7.46 (d, 1 aromatic H ortho to NH2, 3J = 9Hz), 7.99 (s, 1 aromatic H ortho to CO2), 8.79 (broad s, NH2). 13C NMR (75 MHz; Figure S4b): 74.7 (aromatic CI), 112.6 (aromatic CCO2), 119.6 (aromatic C ortho to NH2), 139.4 (aromatic C ortho to COOH), 141.9 (aromatic C para to CO2), 151.4 (aromatic CNH2), 168.8 (C=O).
86% With iodine; acetic acid; potassium hydroxide In water The compound was prepared according to the methoddescribed by Klemme (1940). A solution of anthranilic acid(0.10 mol) in water (500 mL) containing potassiumhydroxide flakes (0.25 mol) was added to a solution ofiodine (0.18 mol) in water (250 mL) having potassium hydroxide (0.61 mol). Glacial acetic acid (100 mL) wasadded to this solution, and the reaction mixture wasimmediately diluted with water (120 mL). The solid thatseparated was filtered, washed with sodium bisulfate(25 mL) and purified by recrystallization from a mixture ofmethanol/water. Yield, 86 percent; m.p., 210 °C.
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 28, p. 4793 - 4796
[2] Synlett, 2014, vol. 25, # 1, p. 148 - 152
[3] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 11, p. 2558 - 2565
[4] Medicinal Chemistry Research, 2016, vol. 25, # 6, p. 1125 - 1139
[5] Synthetic Communications, 2008, vol. 38, # 11, p. 1792 - 1798
[6] Synthetic Communications, 2010, vol. 40, # 23, p. 3506 - 3513
[7] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1989, vol. 28, # 4, p. 321 - 322
[8] Journal of the Chemical Society, 1922, vol. 121, p. 799
[9] Chemische Berichte, 1924, vol. 57, p. 1773
[10] Organic Syntheses, 1939, vol. 19, p. 57[11] Organic Syntheses, 1943, vol. Coll. Vol. II, p. 353
[12] Journal of Organic Chemistry, 1940, vol. 5, p. 227,230, 232
[13] Journal of the Chemical Society, 1953, p. 3711
[14] Bulletin de la Societe Chimique de France, 1942, vol. <5> 9, p. 632
[15] European Journal of Medicinal Chemistry, 2006, vol. 41, # 2, p. 256 - 262
[16] Chemische Berichte, 1914, vol. 47, p. 1938
[17] RSC Advances, 2016, vol. 6, # 113, p. 111767 - 111786
  • 9
  • [ 552-37-4 ]
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Reference: [1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 874 - 881
  • 10
  • [ 95-54-5 ]
  • [ 5851-51-4 ]
  • [ 5326-47-6 ]
YieldReaction ConditionsOperation in experiment
70% for 8 h; Reflux 2-Undecyl-1H-benzo[d]imidazole (11): A mixture of 2 (4.2 gm, 10 mmole) and o-phenylene diamine (1 gm, 10 mmole) in pyridine (40 ml) was refluxed for 8 h. The separated solid was filtered off, dried and recrystallized from light-petroleum ether (b.p. 60-80°C) to give 11 as white crystals mp 90-92°c, yield 70percent. Anal. calcd. for C18H28N2 (272): C, 79.36; H, 10.36; N, 10.28. Found: C, 79.44 H, 10.52 N, 10.11. IR (υ/cm-1): 3166 (NH), 2921, 2849 (CH aliphatic), 1624 (C=N). MS m/z (percent): 272 (M+., 16.8). 1H-NMR (CDCl3) δ (ppm): 12.16 (s, 1H, NH, exchangeable with D2O), 7.56-7.20 (m, 4Harom.), 2.93 (t, 2H), 1.86 (m, 2H), 1.38-1.23 (m, 16H), 0.88 (t, 3H). Acidification of the filtrate with cold concentrated hydrochloric acid afforded brown precipitate which identified as 5-iodoanthranilic acid which recrystallized from benzene mp 220-222°c, yield 30percent. IR (υ/cm-1): 3500 (OH), 3415, 3386 (NH2), 1677 (C=O). 1H-NMR (DMSO-d6) δ (ppm): 14.12 (br.s, 1H, OH, exchangeable with D2O), 8.8 (br.s, 2H, NH2, exchangeable with D2O), 7.92-6.59 (m, 3Harom.).
Reference: [1] Synthetic Communications, 2018, vol. 48, # 18, p. 2391 - 2402
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Reference: [1] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 8, p. 1607 - 1611
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  • [ 118-92-3 ]
  • [ 20776-55-0 ]
  • [ 5326-47-6 ]
Reference: [1] Patent: EP1777215, 2007, A1, . Location in patent: Page/Page column 4-5
[2] Patent: EP1777215, 2007, A1, . Location in patent: Page/Page column 5
[3] Patent: EP1777215, 2007, A1, . Location in patent: Page/Page column 5
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  • [ 134-20-3 ]
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Reference: [1] Journal of the Brazilian Chemical Society, 2018, vol. 29, # 8, p. 1607 - 1611
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  • [ 37960-65-9 ]
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Reference: [1] American Chemical Journal, 1910, vol. 43, p. 405
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  • [ 5326-44-3 ]
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Reference: [1] American Chemical Journal, 1909, vol. 42, p. 500
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