Sodium Hydroxide → (N,N-Dimethylaminoethyl)-2-Iodo-5-Nitro-Benzamide

2-iodo-5-nitro-benzoic acid (3 mmoles) was dissolved in a solution of dry dichloromethane-DMF mixture (v/v 4:1, 5 ml). To the ice-cold solution, was added 6 mmoles of thionyl chloride. The reaction mixture was stirred at room temperature for two hours. The solvent was then evaporated using a rotory evaporator. The residue was dried under vacuum at 50° C. for 30 minutes. The residue was dissolved in dry dichlormethane (5 ml) without any purification. The solution was then cooled to 0° C. To this solution, triethylamine (1 ml) and a solution of N,N-dimethylethylenediamine (3 mmole) in dichloromethane was added. The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was poured into water and basified to pH 12 using 2M NaOH. The organic layer was separated and washed with water, dried over anhydrous magnesium sulfate and concentrated. The (N,N-dimethylaminoethyl)-2-iodo-5-nitro-benzamide compound was separated by silica gel chromatography. The yield was 70%. The melting point was 126-128° C.

1. customThe solvent was then evaporated
2. customa rotory evaporator
3. customThe residue was dried under vacuum at 50° C. for 30 minutes
4. dissolutionThe residue was dissolved in dry dichlormethane (5 ml) without any purification
5. temperatureThe solution was then cooled to 0° C
6. stirringThe reaction mixture was stirred at room temperature for 16 hours
7. customAfter completion of the reaction
8. customThe organic layer was separated
9. washwashed with water
10. dry with materialdried over anhydrous magnesium sulfate
11. concentrationconcentrated
12. customThe (N,N-dimethylaminoethyl)-2-iodo-5-nitro-benzamide compound was separated by silica gel chromatography

ORD-Eintrag

ord-592a3d29d46745a49084b99f74649400

Quelldatensatz

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06225323B1