Reaction #595345

Reaction equation

4-chlorobenzoyl chloride

methyl isocyanatoacetate

triethylamine

→

Methyl 5-(4-chlorophenyl)-1,3-oxazole-4-carboxylate

Solvents

THF

Conditions

Workup

1. 1
   OtherThe solvent is then removed on a rotary evaporator
2. 2
   Washwashed once with 5 ml of water
3. 3
   DryingThe organic phase is dried over magnesium sulfate
4. 4
   Otherthe solvent is removed on a rotary evaporator
5. 5
   Filtrationfiltered off
6. 6
   OtherIt is then recrystallized from about 10 ml of methanol
7. 7
   OtherThis gives needle-shaped crystals which are dried in a drying cabinet at 50° C
8. 8
   OtherA further product fraction is obtained by reprecipitation
9. 9
   Otherafter recrystallization

Procedure

1.40 g (8.00 mmol) of 4-chlorobenzoyl chloride, 1.00 g (10.09 mmol) of methyl isocyanatoacetate and 5.9 ml (42.39 mmol) of triethylamine are dissolved in 15 ml of dry THF and stirred at RT for 48 h. The solvent is then removed on a rotary evaporator. The residue is taken up in 20 ml of ethyl acetate and washed once with 5 ml of water. The organic phase is dried over magnesium sulfate and the solvent is removed on a rotary evaporator. The residue is suspended in 10 ml of cyclohexane and filtered off. It is then recrystallized from about 10 ml of methanol. This gives needle-shaped crystals which are dried in a drying cabinet at 50° C. A further product fraction is obtained by reprecipitation after recrystallization.

Source