Reaction #54763

Reaction equation

4-chlorobutyrylchloride

2-Amino-4-methyloxazole

triethylamine

→

2-(4-Chlorobutyramido)-4-methyloxazole

Yield 23.9%

Solvents

benzene

benzene

Conditions

Workup

1. 1
   workup.ADDITIONAfter the addition the mixture
2. 2
   Temperaturewas heated
3. 3
   Temperatureunder reflux for 2 hours
4. 4
   TemperatureThe mixture was then cooled
5. 5
   Filtrationfiltered
6. 6
   OtherThe filtrate was placed in a separating funnel
7. 7
   Washwashed successively with water (1 × 100 mls.), 10% Na2CO3 (2 × 100 mls.) and water (3 × 100 mls.)
8. 8
   DryingThe organic layer was dried over magnesium sulphate
9. 9
   Otherevaporated under vacuum
10. 10
    OtherThe product was recrystallised from ethyl acetate/hexane

Procedure

2-Amino-4-methyloxazole (5.0 g., 0.0509 mol) was dissolved in dry benzene (100 mls.) and triethylamine (5.70 g., 0.0563 mol) was added. The mixture was stirred vigorously at room temperature and 4-chlorobutyrylchloride (7.88 g., 0.0558 mol) in dry benzene (50 mls.) was added rapidly. After the addition the mixture was heated under reflux for 2 hours. The mixture was then cooled and filtered. The filtrate was placed in a separating funnel and washed successively with water (1 × 100 mls.), 10% Na2CO3 (2 × 100 mls.) and water (3 × 100 mls.). The organic layer was dried over magnesium sulphate and evaporated under vacuum. The product was recrystallised from ethyl acetate/hexane. Wt. = 2.47 g.m.p. 98° C. (Yield = 23.92%).

Source