Dimethylformamide → 5-Iodo-N,N-dimethyl-2-nitrobenzamide

5-Iodo-2-nitrobenzoic acid (15.5 g) was dissolved in chloroform (30 mL). Oxalyl chloride (13.4 g) was added thereto at 0° C., and then DMF (dimethylformamide) (0.1 mL) was further added. The mixture was stirred at room temperature for 2 hours, and then concentrated. After addition of toluene to the residue, the mixture was further concentrated. A solution of the concentrated residue in ethyl acetate (60 mL) was added dropwise to a mixed solution of 50% (w/w) aqueous dimethylamine (7.5 mL) saturated aqueous sodium bicarbonate (60 mL), and toluene (60 mL) under stirring and ice-cooling. The reaction solution was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and saturated brine, and concentrated to give the title compound (15.3 g).

1. concentrationconcentrated
2. additionAfter addition of toluene to the residue
3. concentrationthe mixture was further concentrated
4. additionA solution of the concentrated residue in ethyl acetate (60 mL) was added dropwise to a mixed solution of 50% (w/w) aqueous dimethylamine (7.5 mL) saturated aqueous sodium bicarbonate (60 mL), and toluene (60 mL)
5. stirringunder stirring
6. temperatureice-cooling
7. additionThe reaction solution was diluted with ethyl acetate
8. washwashed with saturated aqueous sodium bicarbonate and saturated brine
9. concentrationconcentrated

ORD record

ord-da66ac0fccd34ec1a7dd9fdb3645536d

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101774B2