Triethylamine → 5H,7H-Imidazo[1,2-C]thiazole-2-carboxaldehyde

The solution of 2-bromo-3-isopropoxypropenal (6.9 g) in dry acetonitrile (326 mL) was added to the solution of crude thiazolidin-4-ylideneamine (3.3 g) in dry acetonitrile (326 mL) at room temperature. The reaction mixture was stirred at room temperature for 19.5 h, added triethylamine (4.9 mL) and then refluxed for 2 h. The reaction mixture was cooled to room temperature and then evaporated under reduce pressure. The residue was dissolved in dichloromethane (300 mL) and washed with 50% potassium carbonate aqueous solution (20 g). After filtration and separation, the aqueous layer was extracted with dichloromethane (50 mL×4). The organic layers were combined, dried (MgSO4) and filtered. The filtrate was evaporated under reduced pressure. The residue was applied to silica gel column chromatography and eluted with CHCl3-MeOH (100:3) to obtain crude 7H-Imidazo[1,2-c]thiazole-2-carbaldehyde as a brown solid. The crude product was re-crystallized twice from CHCl3-n-hexane (1st: 30:5, 2nd: 30:60) at 0° C. to give the required aldehyde as pale brown crystals (Yield: 1.84 g, 15%).

1. temperaturerefluxed for 2 h
2. temperatureThe reaction mixture was cooled to room temperature
3. customevaporated
4. dissolutionThe residue was dissolved in dichloromethane (300 mL)
5. washwashed with 50% potassium carbonate aqueous solution (20 g)
6. filtrationAfter filtration and separation
7. extractionthe aqueous layer was extracted with dichloromethane (50 mL×4)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. customThe filtrate was evaporated under reduced pressure
11. washeluted with CHCl3-MeOH (100:3)
12. customto obtain crude 7H-Imidazo[1,2-c]thiazole-2-carbaldehyde as a brown solid
13. customThe crude product was re-crystallized twice from CHCl3-n-hexane (1st: 30:5, 2nd: 30:60) at 0° C.

ORD record

ord-c96bcaf593ae42ddaa466b06001643e5

Source dataset

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07812014B2