Butyl iodide → N-Butyl-2-methyl-N-(5-methyl-1,3-oxazol-2-yl)propanamide

2-isobutyramido-5-methyloxazole (2.10 g., 0.0124 mol), prepared as above, was dissolved in dry dimethylformamide (10 mls.) and cooled to below 5° C. To this was added sodium hydride (0.70 g., 0.0145 mol.) portionwise, keeping the temperature below 5° C. After the addition, the mixture was stirred for a further 30 minutes at 5° C and then allowed to warm to room temperature. The iodobutane (5.0 g., 0.0271 mol.) was added. The mixture was stirred overnight, the solvent was evaporated under reduced pressure and the residue was partitioned between water (50 mls.) and ether (50 mls.). The organic phase was then washed with 2N HCl (2 × 25 mls.), water (1 × 25 mls.), 10% aqueous sodium carbonate (3 × 25 mls.) and water (3 × 25 mls.). The organic phase was then dried over magnesium sulphate and evaporated under reduced pressure. The residue was distilled from a Kugelrohr, air bath temperature 100° C/0.1 mm. Yield = 1.74 g. (62%).

1. temperaturecooled to below 5° C
2. customthe temperature below 5° C
3. additionAfter the addition
4. temperatureto warm to room temperature
5. stirringThe mixture was stirred overnight
6. customthe solvent was evaporated under reduced pressure
7. customthe residue was partitioned between water (50 mls.) and ether (50 mls.)
8. washThe organic phase was then washed with 2N HCl (2 × 25 mls.), water (1 × 25 mls.), 10% aqueous sodium carbonate (3 × 25 mls.) and water (3 × 25 mls.)
9. dry with materialThe organic phase was then dried over magnesium sulphate
10. customevaporated under reduced pressure
11. distillationThe residue was distilled from a Kugelrohr, air bath temperature 100° C/0.1 mm

ORD record

ord-779687c060d746d49d0a435a16622d54

Source dataset

uspto-grants-1978_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04122183