2-n-Butyl-5-hydroxymethyl-4-iodoimidazole → 2-Butyl-5-formyl-4-iodo-imidazole

A stirred mixture of 174.1 g (0.62 mol) of 2-butyl-5-hydroxymethyl-4-iodoimidazole and 360 g (4.14 mol) of manganese dioxide in 3 liters of methylene chloride was refluxed for 24 hours using a trap to remove water. The hot reaction mixture was filtered through Celite® which was then washed with 4.5 liters of boiling methylene chloride. The combined filtrates were concentrated to dryness, the residue was dissolved twice in 150 mL of methanol and the solution was concentrated to dryness. The residue was dissolved in 130 mL of methanol and chilled. After crystallization had occurred, 700 mL of water was added slowly. The mixture was chilled, the solid was collected by filtration, and washed with water to give 145.2 g (84%) of product; mp 104°-105° C.

1. temperaturewas refluxed for 24 hours
2. customto remove water
3. filtrationThe hot reaction mixture was filtered through Celite® which
4. washwas then washed with 4.5 liters of boiling methylene chloride
5. concentrationThe combined filtrates were concentrated to dryness
6. dissolutionthe residue was dissolved twice in 150 mL of methanol
7. concentrationthe solution was concentrated to dryness
8. dissolutionThe residue was dissolved in 130 mL of methanol
9. temperaturechilled
10. customAfter crystallization
11. addition700 mL of water was added slowly
12. temperatureThe mixture was chilled
13. filtrationthe solid was collected by filtration
14. washwashed with water

ORD record

ord-51e545f2646048dcb1aa50d0e69f7965

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05185351