Hydrochloric Acid → 1H-Benzimidazole-2-methanamine, 1-methyl-, hydrochloride (1:2)

Temperature

-15 °C

Combine N-methyl-o-phenylenediamine (12.2 g, 100 mmol) and glycine (11.3 g, 150 mmol) in 6 N HCl (100 mL). Heat at reflux 90 hours, allow to cool, and concentrate in vacuo to 60 g. Add EtOH (50 mL) and chill at −15° C. Filter the solid and wash with cold 90% EtOH. Dissolve the blue solid in water (30 mL), add EtOH (100 mL) and treat with decolorizing charcoal. Wash the solid with 2:1 EtOH-water and concentrate filtrates in vacuo to 33 g. Add water (15 mL) and warm while adding EtOH (150 mL). Allow to cool, filter, and wash with 90% EtOH to obtain the product as blue flakes. Process the filtrate to obtain a second crop.

1. temperatureHeat
2. temperatureat reflux 90 hours
3. temperatureto cool
4. concentrationconcentrate in vacuo to 60 g
5. filtrationFilter the solid
6. washwash with cold 90% EtOH
7. dissolutionDissolve the blue solid in water (30 mL)
8. additionadd EtOH (100 mL)
9. additiontreat with decolorizing charcoal
10. washWash the solid with 2:1 EtOH-water
11. concentrationconcentrate filtrates in vacuo to 33 g
12. temperatureAdd water (15 mL) and warm
13. additionwhile adding EtOH (150 mL)
14. temperatureAllow to cool
15. filtrationfilter
16. washwash with 90% EtOH
17. customto obtain the product as blue flakes
18. customProcess the filtrate to obtain a second crop

ORD record

ord-e05d2db4f9184db0a6c746885c151958

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06204282B1