2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole Chemical Properties

Melting point:

149-150°C

Boiling point:

494.9±55.0 °C(Predicted)

Density 

1.41

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

10.60±0.10(Predicted)

form 

Crystalline Powder

color 

White to Pale Orange

λmax

292nm(EtOH)(lit.)

InChI

InChI=1S/C16H14F3N3OS/c1-10-13(20-7-6-14(10)23-9-16(17,18)19)8-24-15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)

InChIKey

CCHLMSUZHFPSFC-UHFFFAOYSA-N

SMILES

C1(SCC2=NC=CC(OCC(F)(F)F)=C2C)NC2=CC=CC=C2N=1

CAS DataBase Reference

103577-40-8(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29309090

2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole Usage And Synthesis

Chemical Properties

Pale Yellow Solid

Uses

Lansoprazole Sulfide (Lansoprazole EP Impurity C; USP Impurity B) is a metabolite of Lansoprazole, as gastric pump inhibitor.

Synthesis

2-Chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine (91 g, 0.38 mol) and 1H-benzo[d]imidazole-2-thiol (57 g, 0.38 mol) were used as raw materials, suspended in methanol (1 L), and benzyltributylammonium bromide (2.15 g) was added as a phase transfer catalyst. A 30% NaOH solution (65 mL) was added slowly and dropwise over a period of 1 h, followed by stirring the reaction for 2 h at room temperature. Upon completion of the reaction, water (300 mL) was added to the reaction mixture and stirring was continued for 30 min. The mixture was cooled to 10 °C and the pH was adjusted to 9 with 35% HCl, at which point the target product 2-(((3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)methyl)thio)-1H-benzo[d]imidazole precipitated as a precipitate. The precipitate was collected by filtration and washed sequentially with 50% methanol and water. Finally, the product was dried under vacuum at 50 °C to give 129 g in 96% yield.

References

[1] Organic Process Research and Development, 2013, vol. 17, # 10, p. 1272 - 1276
[2] Patent: CN106543146, 2017, A. Location in patent: Paragraph 0025; 0031; 0032; 0041; 0045; 0049; 0053-0069
[3] Synthetic Communications, 2002, vol. 32, # 8, p. 1211 - 1217

2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole(103577-40-8)Related Product Information

• Kresoxim-methyl
• Methyl acetate
• Methyl salicylate
• METSULFURON METHYL
• 5-Amino-2-methylpyridine
• 4-Methylpyridine
• Ethoxymethylenemalononitrile
• Benzimidazole
• ISOMETHIOZIN
• 2-Chloro-5-chloromethylpyridine
• Azamethiphos
• Tribenuron methyl
• 2,6-Lutidine
• 2-Hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride
• Thiophanate-methyl
• Methyl
• 4-Nitro-2,3-lutidine-N-oxide
• 2-Chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride