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[ CAS No. 152628-03-0 ]

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CAS No. :152628-03-0 MDL No. :MFCD06656215
Formula : C12H14N2O2 Boiling Point : 491.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :218.25 g/mol Pubchem ID :10262831
Synonyms :

Safety of [ 152628-03-0 ]

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

Application In Synthesis of [ 152628-03-0 ]

  • Upstream synthesis route of [ 152628-03-0 ]
  • Downstream synthetic route of [ 152628-03-0 ]

[ 152628-03-0 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 152628-01-8 ]
  • [ 152628-03-0 ]
YieldReaction ConditionsOperation in experiment
96.4% at 70 - 100℃; Example 4:4-butyramido-3-methyl-5-nitro methyl benzoate (II) (10 gm, 0.036 moles), was suspended in water (60 ml) and heated to 70-80 °C. A suspension of sodium dithionite (21.75 gm, 0.124 moles) in water (60 ml) was added gradually to the above mass and the temperature is raised to 90-100 °C. After the reaction complies, the pH of the reaction mixture was adjusted to 10-11 and continued to stir at same temperature until the methyl-4-methyl-2-propyl-lH-benzimidazole-6-carboxylate disappears in TLC. Then the pH of the reaction mass adjusted to pH 6-6.5. The solid obtained was filtered and dried at 45-50 °C to afford 2-n-propyl-4-methyl-6- carboxy benzimidazole (7.5 gms, Yield: 96.4 percent).
Reference: [1] Patent: WO2012/28925, 2012, A2, . Location in patent: Page/Page column 18
[2] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[4] Patent: WO2012/28925, 2012, A2,
[5] Organic Process Research and Development, 2007, vol. 11, # 1, p. 81 - 85
[6] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 2
  • [ 201230-82-2 ]
  • [ 215239-53-5 ]
  • [ 152628-03-0 ]
YieldReaction ConditionsOperation in experiment
89% With water; potassium carbonate; triphenylphosphine In 1,4-dioxane at 60 - 100℃; for 49.5 h; Autoclave 4-Methyl-2-propylbenzimidazole-6-carboxylic acid (I; R1 = CH3, R2 = W-C3H7, Q1 = COOH) 6-Bromo-4-methyl-2-propylbenzimidazole (7.O g) was dissolved in a mixture of 1,4-dioxane (32.8 g) and water (32.8 g) in an autoclave. Subsequently, potassium carbonate (7.33 g), tri- phenylphosphine (450 mg) and palladium dichloride (46.6 mg) were added to the solution. The reaction mixture was heated to 60 °C and carbon monoxide (9 bar) was added at 60 °C. The reaction mixture was further heated to 100 0C during 90 min. After reaching the reaction temperature the CO pressure was increased to 14 bar and the reaction mixture was stirred under these conditions for another 48 h. The reaction mixture was then cooled to 25 °C and active charcoal (1.6 g) was added. After filtration the yield of the reaction was determined via HPLC. 7.1 g (89percent) of the product 4-methyl-2-propylbenzimidazole-6-carboxylic acid were obtained.
Reference: [1] Patent: WO2010/81670, 2010, A2, . Location in patent: Page/Page column 22
  • 3
  • [ 37901-95-4 ]
  • [ 24964-76-9 ]
  • [ 152628-03-0 ]
YieldReaction ConditionsOperation in experiment
94.4% With methanesulfonic acid In N,N-dimethyl-formamide at 70℃; for 9 h; 5 g of compound 12 was added to 30 mL of DMF, 4.1 g of triethyl orthobutyrate and 0.5 g of methanesulfonic acid were added, and the mixture was heated with stirringTo 70 , the reaction 9h. The reaction was monitored by HPLC to control the remaining amount of raw materials to be 0.5percent or less of the initial amount. Ice bath cooling crystallization 2h, vacuum suction filtration. The wet product was dried at 80 ° C to give 6.2 g of white solid compound 2 as a white solid, yield 94.4percent.
Reference: [1] Patent: CN103755641, 2017, B, . Location in patent: Paragraph 0015; 0016; 0038; 0039; 0043
  • 4
  • [ 152628-00-7 ]
  • [ 152628-03-0 ]
YieldReaction ConditionsOperation in experiment
80% With water; sodium hydroxide In methanol at 80℃; Example 1:Methyl-4-methyl-2-propyl-lH-benzimidazole-6-carboxylate (40 gms, 0.172 moles) was suspended in methanol (200 ml) and stirred for few minutes. Sodium hydroxide (13.76 gms, 0.344 moles) dissolved in water (50 ml) was added to the reaction mass and the temperature is maintained at 80°C. After completion of the reaction, methanol was evaporated under reduced pressure and water (100 ml) was added to the crude mass at 5-10 °C. Then adjusted the pH of the crude mass to 6- 6.5 and the obtained solid was filtered. The solid was washed with water and dried at temperature of 45-50 °C under vacuum (700 mm) to yield 2-n-propyl-4-methyl- 6-carboxy benzimidazole (30gms, Yield: 80 percent).
Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
[2] Patent: WO2012/28925, 2012, A2, . Location in patent: Page/Page column 17
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[4] Patent: EP2327690, 2011, A1, . Location in patent: Page/Page column 83-84
[5] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 5
  • [ 153036-72-7 ]
  • [ 152628-03-0 ]
YieldReaction ConditionsOperation in experiment
30% With hydrogenchloride; water In 1,4-dioxane at 100℃; for 16 h; Example 97-methyl-2-propyl-3H-benzimidazole-5-carboxylic acid (I1 R1 = CH3, R2 = /7-C3H7,R3 = COOH)The mixture of 7-methyl-2-propyl-3H-benzoimidazole-5-carbonitrile (250 mg, 1 mmol, 1.0 eq.), aqueous hydrochloric acid (36percent, 2.5 ml_, 29 mmol, 2.3 eq.) in 1 ,4-dioxane (2.5 ml_) was heated to 100 0C for 16 h. After removal of volatiles, the concentrate was diluted with methanol, and decolorized with activated carbon to give a white solid. Yield: 85 mg (30percent). The spectral data of this product were identical to that of commercial product:1H NMR (400 MHz, DMSO-d6): δ 12.42 (s, 1 H), 7.82 (s, 1 H), 7.56 (s, 1 H), 2.80 (t, J= 7.4 Hz, 2H), 2.50 (s, 3H), 1.79 (qd, J= 7.4 Hz, J = 7.32 Hz, 2H), 0.94 (t, J= 7.32 Hz, 3H). 13C NMR (100 MHz, DMSO-d6): δ 168.6, 157.5, 124.1 , 123.3, 31.0, 21.4, 17.1 , 14.2.
Reference: [1] Patent: WO2010/149360, 2010, A1, . Location in patent: Page/Page column 11
  • 6
  • [ 110-62-3 ]
  • [ 37901-94-3 ]
  • [ 152628-03-0 ]
YieldReaction ConditionsOperation in experiment
37% With sodium dithionite In ethanol; water at 70℃; for 2 h; A mixture of 4-amino-3-methyl-5-nitrobenzoic acid (0.98 g, 5 mmol, 1 eq.), sodium dithionite (2.47 g, 14 mmol, 2.8 eq.), /7-butyraldehyde (0.38 g, 5 mmol, 1.0 eq.), ethanol (15 mL) and water (15 mL) was heated to 70 0C for 2 h. The reaction mixture was cooled to room temperature and ethanol was removed by rotary evaporator. The solid precipitated was washed with water, collected by filtration and dried under vacuum to give an off-white solid. Yield: 0.41 g (37percent).1H NMR (400 MHz, DMSO-ofe): δ 12.42 (s. 1 H), 7.82 (s, 1 H), 7,56 (s, I H), 2.80 (t, J= 7 A Hz, 2H), 2.50 (s, 3H), 1.79 (qd, J= 7.4 Hz, J= 7.32 Hz, 2H), 0.94 (t, J= 7.32 Hz, 3H). "C NMR (100 MHz, DMSO-αfc): δ 168.6, 157.5, 124.1 , 123.3, 31.0, 21.4, 17.1 , 14.2.
Reference: [1] Patent: WO2010/149359, 2010, A1, . Location in patent: Page/Page column 12
  • 7
  • [ 675882-71-0 ]
  • [ 152628-03-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[3] Patent: WO2006/44754, 2006, A2, . Location in patent: Page/Page column 25-26
[4] Organic Process Research and Development, 2007, vol. 11, # 1, p. 81 - 85
[5] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 8
  • [ 18595-14-7 ]
  • [ 152628-03-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 9
  • [ 301533-59-5 ]
  • [ 152628-03-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 10
  • [ 18595-14-7 ]
  • [ 141-75-3 ]
  • [ 152628-03-0 ]
Reference: [1] RSC Advances, 2017, vol. 7, # 42, p. 26401 - 26410
  • 11
  • [ 1235469-21-2 ]
  • [ 152628-03-0 ]
Reference: [1] Patent: WO2010/81670, 2010, A2, . Location in patent: Page/Page column 22 - 23
  • 12
  • [ 3113-71-1 ]
  • [ 152628-03-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
  • 13
  • [ 24078-21-5 ]
  • [ 152628-03-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2003, vol. 40, # 6, p. 1107 - 1112
  • 14
  • [ 884330-16-9 ]
  • [ 152628-03-0 ]
Reference: [1] Patent: WO2006/44754, 2006, A2, . Location in patent: Page/Page column 29
  • 15
  • [ 2486-70-6 ]
  • [ 152628-03-0 ]
Reference: [1] Patent: CN103755641, 2017, B,
  • 16
  • [ 99-12-7 ]
  • [ 152628-03-0 ]
Reference: [1] Patent: CN107118161, 2017, A,
  • 17
  • [ 65151-56-6 ]
  • [ 152628-03-0 ]
Reference: [1] Patent: CN107118161, 2017, A,
  • 18
  • [ 25148-68-9 ]
  • [ 152628-03-0 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
77.4%
Stage #1: at 70 - 135℃; for 13.5 h;
Stage #2: With ammonia In water at 30 - 90℃; for 1 h;
4-Methyl-2-n-propyl-lH-benzimidazole-6-carboxylic acid (50 gms) is suspended in Poly phosphoric acid (300 gms), temperature is raised and maintained for 30 min at 70 - 750C, N-Methyl-o-phenylenediamine dihydrochloride. (45 gms) is added lot wise over 2 hrs and maintained at temperature of 70 - 750C for lhr. The temperature of the reaction mass is raised and maintained for 10 hrs at 130 - 1350C. Mass temperature is cooled to 7O0C, water (600 ml) is added slowly at temperature of 60 - 9O0C. Temperature of the reaction mass is cooled to 3O0C, pH is adjusted to 8.0 - 8.5 with aqueous ammonia solution. EPO <DP n="12"/>Temperature of the reaction mass is raised, maintained at 50- 550C for 1 hr, filter the solid, wet cake is washed with hot water (200 ml) and unload the wet cake. The above wet cake suspended in water (900 ml), temperature is raised and mixed for 1 hr at 50 - 550C. Filtered the solid, washed with hot water (100 ml) and dried the wet cake at temperature of 70 - 750C till constant weight. The above dry material is suspended in methanol (260 ml), and temperature is raised to 45 - 5O0C, charcoal (6.5 gms) is added and mixed for about 30 min. Insolubles are filtered through hyflow bed, washed the bed with hot methanol (60 ml), collect and cooled the filtrate to 250C. Water (160 ml) is added slowly to the filtrate at temperature of 25 - 350C, Mass temperature is raised, maintained for 1 hr at reflux temperature. Reaction mass temperature is cooled, maintained for 2 hrs at 0 - 50C. The solid obtained is filtered, wet cake is washed with methanol (60 ml), the wet cake is dried at temperature of 70 - 750C till becomes constant weight. The dry weight of 4-Methyl-6(l -methyl benzimidazol-2-yl)-2-n-propyl IH- benzimidazole is 54 gms (Yield 77.4percent). Water content by KF is 5.85percent.
Reference: [1] Patent: WO2007/10558, 2007, A1, . Location in patent: Page/Page column 5; 10-11
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
[3] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 161 - 178
  • 19
  • [ 4760-34-3 ]
  • [ 152628-03-0 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: at 75 - 145℃;
Stage #2: With sodium hydroxide In water
Example 2; Variant 2; Methanesulphonic acid is heated to about 80° C. At a temperature of 75° C. to 85° C., 2-propyl-4-methyl-1H-benzimidazole-6-carboxylic acid is added. Then at 85° C. to 95° C. N-methyl-o-phenylene-diamine is added.The mixture is heated to110° C. to 130° C. and phosphorus pentoxide is metered in until an internal temperature of not more than 160° C. is reached. Then the mixture is stirred for 3 hours at a maximum temperature of 145° C. It is cooled to <100° C. and water is metered into the reaction mixture. 50percent sodium hydroxide solution is added at <100° C. until a pH of less than 3 is obtained.Finally, treatments with charcoal are carried out at <100° C.At a temperature of <80° C. isopropanol is added and the mixture is adjusted with sodium hydroxide solution to a pH between 4.5 and 7. The aqueous phase is separated off. In order to precipitate dimethyl-2'-propyl-2,5'-bi-1H-benzimidazole water is metered in, the contents of the apparatus are cooled to at least 40° C. for technical reasons and the product is isolated.Yield: 78-90percent of theoryHPLC purity: >99.5percent.
Reference: [1] Patent: US2011/190508, 2011, A1, . Location in patent: Page/Page column 2
[2] Journal of Chemical Research, 2010, # 2, p. 95 - 97
[3] Synthetic Communications, 2009, vol. 39, # 23, p. 4149 - 4157
[4] Patent: JP2015/160810, 2015, A, . Location in patent: Paragraph 0051; 0052
  • 20
  • [ 81684-80-2 ]
  • [ 152628-03-0 ]
  • [ 152628-02-9 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: at 70 - 130℃;
Stage #2: With ammonia In water; ethyl acetate for 3 h; Cooling with ice
Example 1:Orthophosphoric acid (210 gms) was taken in round bottomed flask and Ρ205 (210 gms) was added in portions with vigorous stirring. (Note: Sharp increase in temperature > 200 °C). The above mass is allowed to cool to 70 °C and 2-n-propyl- 4-methyl-benzimidazole-6-carboxylic acid (70 gms, 0.321 mol) was added slowly. Then N-methylbenzene-l,2-diamine hydrochloride (62.3 gms, 0.321 mol) was added in small portions at same temperature and then the temperature was raised to 125-130 °C. After completion, reaction was quenched with ice cold water (1 Lt), adjusted pH of the reaction mixture to 9-10 by the addition of aqueous ammonia solution. Obtained solid was filtered and washed with cold water until the pH of the filtrate becomes neutral. Then the crude solid was washed with hot water until colorless filtrate was observed. The crude solid was boiled in ethyl acetate (700 ml) for 2-3 hrs. The reaction mass was cooled and the suspension was filtered off and dried to yield 2-n-propyl-4-methyl-6-(l-methylbenzimidazol-2-yl)-lH- benzimidazole (V) (80 gms, Yield : 82 percent).
Reference: [1] Patent: WO2012/28925, 2012, A2, . Location in patent: Page/Page column 19
[2] Patent: WO2006/44754, 2006, A2, . Location in patent: Page/Page column 26
  • 21
  • [ 81684-80-2 ]
  • [ 152628-03-0 ]
  • [ 884330-09-0 ]
  • [ 884330-18-1 ]
  • [ 884330-17-0 ]
  • [ 152628-02-9 ]
Reference: [1] Organic Process Research and Development, 2007, vol. 11, # 1, p. 81 - 85
  • 22
  • [ 152628-03-0 ]
  • [ 144701-48-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 25, p. 4040 - 4051
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