103312-62-5

Basic information

• Product Name: 2-[(4-Chloro-3-Methyl-2-Pyridinyl-methyl)thio]-1H-Benzimidazole
• Synonyms: 2-[(4-Chloro-3-Methyl-2-Pyridinyl-methyl)thio]-1H-Benzimidazole;2-[(4-Choloro-3-methyl-2-pyridinyl methyl)thio]-1H-benzimidazole;4-Desmethoxypropoxyl-4-chloro Rabeprazole Sulfide;Lansoprazole EP IMpurity F Sulfide;2-(((4-Chloro-3-methylpyridin-2-yl)-methyl)thio)-1H-benzo[d]imidazole;Lansoprazole impurity N;Rabeprazole Impurity 4;Rabeprazole sodium Impurity I
• CAS NO: 103312-62-5
• Molecular Formula: C₁₄H₁₂ClN₃S
• Molecular Weight: 289.78318
• Product Categories: API intermediates;Aromatics;Heterocycles;Impurities;Sulfur & Selenium Compounds
• Mol File: 103312-62-5.mol

Chemical Properties

• Melting Point: 155-160 °C(Solv: ethanol (64-17-5))
• Boiling Point: 495.38 °C at 760 mmHg
• Flash Point: 253.397 °C
• Appearance: /
• Density: 1.4 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.707
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 10.59±0.10(Predicted)
• CAS DataBase Reference: 2-[(4-Chloro-3-Methyl-2-Pyridinyl-methyl)thio]-1H-Benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-Chloro-3-Methyl-2-Pyridinyl-methyl)thio]-1H-Benzimidazole(103312-62-5)
• EPA Substance Registry System: 2-[(4-Chloro-3-Methyl-2-Pyridinyl-methyl)thio]-1H-Benzimidazole(103312-62-5)

Safety Data

• Hazardous Substances Data: 103312-62-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

A process impurity of Rabeprazole (R070500).

InChI:InChI=1/C14H12ClN3S/c1-9-10(15)6-7-16-13(9)8-19-14-17-11-4-2-3-5-12(11)18-14/h2-7H,8H2,1H3,(H,17,18)

Upstream product

• 134469-07-1 Benzimidazol-2-thiol 
• 59886-84-9 (4-chloro-3-methylpyridin-2-yl)methyl acetate 
• 59886-85-0 2-hydroxymethyl-4-chloro-3-methylpyridine 
• 59886-90-7 4-chloro-2,3-dimethylpyridine-N-oxide 
• 37699-43-7 2,3-dimethyl-4-nitropyridine N-oxide 
• 152402-97-6 2-chloromethyl-4-chloro-3-methylpyridine hydrochloride 

Downstream Products

• 1187926-83-5 2-[(R)-[(4-chloro-3-methyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole 
• 117976-47-3 LY 307640 sulfone 
• 924663-37-6 2-[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole 
• 117977-21-6 rabeprazole sulfide 
• 168167-42-8 2-[(RS)-[(4-chloro-3-methylpyridin-2-yl)methyl]sulfinyl]-1H-benzimidazole 

Relevant articles and documents

Synthetic studies connected with the preparation of H+/K +-ATPase inhibitors rabeprazole and lansoprazole

Synthesis of lansoprazole and rabeprazole using common intermediates is devised. The common intermediates, 2-[(4-nitro-3-methylpyridin-2-yl) methanesulfanyl]-1H-benzoimidazole and 2-[(4-chloro-3-methyl-pyridin-2-yl) methanesulfanyl]-1H-benzoimidazole, were prepared in several ways.

Identification and synthesis of potential impurities of rabeprazole sodium

Rabeprazole sodium (1, Achiphex) is a gastric proton pump inhibitor. It causes dose-dependent inhibition of acid secretion and is useful as an anti-ulcer agent. In the process for the preparation of 1, two potential unknown impurities were identified in HPLC at levels ranging from 0.05-0.8%. Based on mass spectral data vide LC-MS, the two impurities were characterized as 2-{[(4-chloro-3-methyl-2-pyridinyl) methyl] sulfinyl}-1H-bezimidazole (2, chloro analogue of rabeprazole) and 2-[{(4-methoxy-3-methyl-2-pyridinyl)methyl} sulfinyl]-1H-benzimidazole (3, methoxy analogue of rabeprazole). The structures were unambiguously established by independently synthesizing them and co-injecting in HPLC. To our knowledge, the compounds 2 and 3 have not been reported as process impurities elsewhere.