Dimethyl Sulfoxide → HCID 20077574, compound

A solution of dimethyl sulphoxide (0.49 ml, 7.74 mmol) in dichloromethane (2.5 ml) was added dropwise to a solution of oxalyl chloride (0.3 ml, 3.78 mmol) in dichloromethane (15 ml) at -78° C. with stirring under argon. After effervescence had ceased (15 min), a solution of the product of step (ii) (313 mg, 1.72 mmol) in dichloromethane (7.5 ml) was added dropwise. The solution was stirred for 15 minutes before triethylamine (2.3 ml, 19 mmol) was added slowly. After a further 15 minutes the solution was allowed to warm to room temperature, stirred for 30 minutes and then quenched by the addition of a saturated aqueous solution of sodium bicarbonate (10 ml). The mixture was extracted with ethyl acetate (3×10 ml). The extracts were washed with brine (1×10 ml), dried (MgSO4) and concentrated. The residue was purified by column chromatography, eluting with 10% methanol/dichloromethane (v/v), to give 1-hexyl-imidazole-5-carboxaldehyde (280 mg, 90% yield) as an oil; NMR: 0.8-0.95(3H,m), 1.2-1.4(6H,m), 1.68-1.9(2H,m), 4.29(2H,t,J=7. Hz), 7.65(1H,s), 7.80(1H,s), 9.74(1H,s).

1. custom(15 min)
2. additionwas added slowly
3. stirringstirred for 30 minutes
4. customquenched by the addition of a saturated aqueous solution of sodium bicarbonate (10 ml)
5. extractionThe mixture was extracted with ethyl acetate (3×10 ml)
6. washThe extracts were washed with brine (1×10 ml)
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customThe residue was purified by column chromatography
10. washeluting with 10% methanol/dichloromethane (v/v)

ORD record

ord-3aecdfa9313f477eb3ac0f3106a8f5e1

Source dataset

uspto-grants-1993_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05219874