Diethylamine → N,N-diethyl-4-formylbenzamide

To a suspension of 4-carboxybenzaldehyde (30 g, 0.2 mole) in 100 ml of toluene was added SOCl2 (97 ml, 1.3 moles) at 60° C. The reaction was heated until gas evolution ceased followed by evaporation to dryness with toluene (3×50 mL) This yielded a residue, which was dissolved in CH2Cl2 (200 mL). To this solution, cooled in an ice bath while stirring, was added diethylamine (50 mL). Stirring was continued for one hour and then the mixture heated at reflux for a further hour. After cooling, the mixture was washed successively with H2O, 2 N HCl, H2O then 2 N NaOH and finally with H2O. The solution was dried over MgSO4, filtered and concentrated to dryness yielding 41 g of oil. Distillation at 140-150° C./1.5 torr gave 36.9 g, 90% of INTERMEDIATE 1.

1. temperatureThe reaction was heated until gas evolution
2. customceased followed by evaporation to dryness with toluene (3×50 mL)
3. customThis yielded a residue, which
4. temperatureTo this solution, cooled in an ice bath
5. stirringStirring
6. temperaturethe mixture heated
7. temperatureat reflux for a further hour
8. temperatureAfter cooling
9. washthe mixture was washed successively with H2O, 2 N HCl, H2O
10. dry with materialThe solution was dried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated to dryness

ORD record

ord-013f471b89d0404c84bc2bafe009cbd2

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07396834B2