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[ CAS No. 136304-93-3 ] {[proInfo.proName]}

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Chemical Structure| 136304-93-3
Chemical Structure| 136304-93-3
Structure of 136304-93-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 136304-93-3 ]

CAS No. :136304-93-3 MDL No. :MFCD26390687
Formula : C14H10ClN Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 227.69 Pubchem ID :-
Synonyms :

Safety of [ 136304-93-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 136304-93-3 ]

* 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 [ 136304-93-3 ]
  • Downstream synthetic route of [ 136304-93-3 ]

[ 136304-93-3 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 136304-93-3 ]
  • [ 152628-02-9 ]
  • [ 144701-48-4 ]
YieldReaction ConditionsOperation in experiment
120 g
Stage #1: With sodium hydroxide In water for 0.166667 h;
Stage #2: With tetra(n-butyl)ammonium hydrogensulfate In water at 80 - 85℃; for 4 h;
Stage #3: With sodium hydroxide In butan-1-ol at 123 - 126℃; for 24 h;
EXAMPLE 1 4′-[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazol-1-ylmethyl]biphenyl-2-carboxylic acid [0018] In a 2 litre reaction flask was added 400 ml methylene chloride, followed by 100 gm of 2-cyano-4′-methyl biphenyl. The reaction mass was stirred to get a clear solution and cooled to 20° C. Chlorine gas was sparged into the reaction mass for a period of 15 hours till completion of the reaction. The reaction was monitored by TLC using mobile phase n-hexane: ethyl acetate (8:2). The excess chlorine from the reaction mass was removed by flushing with nitrogen. The solvent was distilled out completely by distillation at atmospheric pressure and removal of the final traces under vacuum. To the residual mass, 500 ml of methyl isobutyl ketone was added. The reaction mass was stirred and washed with a solution of 300 ml of 5percent sodium bicarbonate solution. The lower aqueous layer was separated and the upper organic layer was washed with 300 ml water. The lower aqueous layer was separated. To the organic layer containing 4-chloromethyl-2′-cyanobiphenyl, the compound 2-n-propyl-4-methyl-6-(1′-methylbenzimidazol-2′-yl)benzimidazole was added, followed by a solution of 40 gm sodium hydroxide in 300 ml water. The reaction mass was stirred for 10 minutes and 10 gm of tetrabutyl ammonium hydrogen sulphate was added. The reaction mass was heated to 80° C. and maintained at 80 to 85° C. for 4 hours. [0019] The completion of the reaction was monitored by TLC using mobile phase chloroform: methanol (9:1). After completion of reaction, the lower aqueous layer was separated. The solvent was distilled out till mass temperature 120° C. and final traces were removed completely under vacuum. To the residual mass, 50 ml of n-butanol was added and the solvent distilled out under vacuum below 100° C. to remove all traces of methyl isobutyl ketone. The residue was dissolved in 750 ml of n-butanol and 83 gm sodium hydroxide added. The reaction mass was heated to reflux and maintained for 24 hours at 123 to 126° C. The completion of the reaction was monitored by TLC using mobile phase chloroform:methanol (9:1). [0020] The solvent was distilled out at atmospheric pressure till the mass temperature reached 140° C. The residual mass was cooled to 100° C. and 300 ml water was added. The solvent was distilled out azeotropically till the mass temperature reached 120° C. To the reaction mass 750 ml of water was added, the solution warmed to 80° C. The pH of the reaction mass was adjusted to 8.0 with hydrochloric acid. Finally the pH was adjusted to 6.0 with acetic acid, and the reaction mass maintained at 80 to 85° C. for one hour. The product obtained was filtered, washed with water and dried to yield 120 gm of 4′-[2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazol-1-ylmethyl]biphenyl-2-carboxylic acid, which can be purified as per the procedure described mentioned in Example 5.
Reference: [1] Patent: US2015/197495, 2015, A1, . Location in patent: Paragraph 0018; 0019; 0020
[2] Patent: CN104768936, 2017, B, . Location in patent: Paragraph 0134-0135
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