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

1. temperaturewas refluxed for 24 hr
2. customto remove water
3. filtrationThe hot reaction mixture was filtered through a Celite® pad which
4. washwas then washed with 4.5 L of boiling methylene chloride
5. concentrationThe combined filtrates were concentrated to dryness
6. dissolutionThe residue was dissolved twice in 150 ml of methanol
7. concentrationeach time the 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
15. customdried

ORD record

ord-de21b1de13124c589802a272f7412025

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05728842