تفاعل #54769

معادلة التفاعل

2-isobutyramido-5-methyloxazole

sodium hydride

iodobutane

→

2-(N-butyl-isobutyramido)-5-methyloxazole

المذيبات

dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to below 5° C
2. 2
   أخرىthe temperature below 5° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   درجة الحرارةto warm to room temperature
5. 5
   workup.STIRRINGThe mixture was stirred overnight
6. 6
   أخرىthe solvent was evaporated under reduced pressure
7. 7
   أخرىthe residue was partitioned between water (50 mls.) and ether (50 mls.)
8. 8
   غسيلThe 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. 9
   تجفيفThe organic phase was then dried over magnesium sulphate
10. 10
    أخرىevaporated under reduced pressure
11. 11
    workup.DISTILLATIONThe residue was distilled from a Kugelrohr, air bath temperature 100° C./0.1 mm

الإجراء التجريبي

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%).

المصدر