Reacción #7296

Ecuación de reacción

acetic anhydride

4-formylbenzonitrile

N-acetylglycine

sodium acetate

→

4-(2-Methyl-5-oxooxazol-4-ylidenemethyl)benzonitrile

Disolventes

Acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for 1 h
2. 2
   workup.STIRRINGwith stirring
3. 3
   Temperaturacooling
4. 4
   workup.STIRRINGThe mixture was stirred at 20° C. for another 1 h
5. 5
   OtroTo isolate the product
6. 6
   Lavadowashed with deionized water (75 l), isopropanol (40 l) and methyl-tert-butylether (75 l)
7. 7
   OtroThe product was dried under reduced pressure at 40° C

Procedimiento

Acetone (80.0 l) was introduced into a mixture of 4-formylbenzonitrile (15.0 kg, 114.5 mol), N-acetylglycine (19.2 kg, 162.4 mol) and anhydrous sodium acetate (9.4 kg, 114.5 mol) followed by introduction, with stirring, of acetic anhydride (35.0 l, 370.5 mol). The reaction mixture was stirred under reflux for 1 h. The resulting thin yellow suspension was cooled to 50° C. and ice-water (200 l) was added as quickly as possible, with stirring and cooling. The mixture was stirred at 20° C. for another 1 h. To isolate the product, the yellow suspension was pressed onto a centrifuge and washed with deionized water (75 l), isopropanol (40 l) and methyl-tert-butylether (75 l). The product was dried under reduced pressure at 40° C. Yield 18.17 kg (85.7 mol, 75.2% of theory). M.p.: 192–193° C.; MS (DCl): m/z=213 [M+H+]; 1H-NMR (DMSO-d6): δ=2.42 (s, 3H), 7.30 (s, 1H), 7.96 (d, 2H), 8.33 (d, 2H).

Fuente