3689-76-7 Usage
Originator
Diamyceline,Diamant
Manufacturing Process
The first method synthesis of 1-p-chlorobenzyl-2-methylbenzimidazole:
26.4 g of 2-methylbenzimidazole are dissolved in 350 ml of dioxane, 10 g of
sodium amide are added there to. After about 5 min 41,2 g of pchlorobenzylbromide are added to the resulting mixture which is then boiled
under reflux for 6 hours. Dioxane is removed by distillation. The residue is
triturated with dilute hydrochloric acid. The resulting crystalline mass
representing the crude hydrochloride of 1-p-chlorobenzyl-2-
methylbenzimidazole is filtered off by suction and recrystallized from water.
On cooling, colorless crystals are obtained which are dissolved in hot water.
Dilute ammonia solution is added to the resulting aqueous solution to render
it weakly alkaline. The base of 1-p-chloro-benzyl-2-methylbenzimidazole
precipitates, first in liquid form, and gradually solidifies to a white mass of its
hydrate. After recyrstallization from aqueous ethanol, the product has a
melting point of 67-68°C. The base of 1-p-chlorobenzyl-2-
methylbenzimidazole distills in the form of a colorless oil at 240-242°C/12
mm. Its hydrate of the melting point 67-68°C is obtained by trituration with
water.
The second method of synthesis of 1-p-chlorobenzyl-2-methylbenzimidazole:
23.3 g of p-chlorobenzyl-o-phenylenediamine are boiled under reflux with 75
ml of glacial acetic acid for 3 hours. Most of the acetic acid is then removed
by distillation. Dilute sodium hydroxide solution is added to the residue to
render it weakly alkaline. The resulting base of 1-p-chlorobenzyl-2-
methylbenzunidazole is purified as such by recrystallization from aqueous
ethanol. It may also be converted into its hydrochloride which is then worked
up as described hereinabove in the first method of synthesis.
Therapeutic Function
Antifungal
Check Digit Verification of cas no
The CAS Registry Mumber 3689-76-7 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,8 and 9 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 3689-76:
(6*3)+(5*6)+(4*8)+(3*9)+(2*7)+(1*6)=127
127 % 10 = 7
So 3689-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C15H13ClN2/c1-11-17-14-4-2-3-5-15(14)18(11)10-12-6-8-13(16)9-7-12/h2-9H,10H2,1H3
3689-76-7Relevant articles and documents
Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles
An, Jie,Lai, Zemin,Li, Hengzhao,Peng, Mengqi,Sun, Yanhao,Yan, Zihan,Yang, Ruoyan,Zhang, Yuntong
, p. 748 - 753 (2022/02/02)
We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc
Rhodium(III)-Catalyzed Directed C?H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles
Chen, Yanyu,Zhang, Rong,Peng, Qiujun,Xu, Lanting,Pan, XianHua
supporting information, p. 2804 - 2808 (2017/10/20)
An efficient rhodium-catalyzed direct C?H amidation of N-nitrosoanilines with 1,4,2-dioxazol-5-ones as amidating agents has been developed. This method featured mild reaction conditions, a wide substrate scope and satisfactory yields. Besides, the amidated products could be readily converted to pharmaceutically valuable 1,2-disubstituted benzimidazoles via an HCl-mediated deprotection/cyclization process in one pot.
Benzimidazoles as new potent and selective DP antagonists for the treatment of allergic rhinitis
Beaulieu, Christian,Wang, Zhaoyin,Denis, Danielle,Greig, Gillian,Lamontagne, Sonia,O'Neill, Gary,Slipetz, Deborah,Wang, Jennifer
, p. 3195 - 3199 (2007/10/03)
A series of 2-substituted N-benzyl benzimidazole containing molecules has been synthesized and its structure-activity relationship for the human DP receptor has been evaluated. Selective DP antagonists with nanomolar potency for the DP receptor were identified in this novel series of benzimidazoles.
