Ammonia → HCID 22096854, compound

3-[N,N-Bis(2-chloroethyl)amino]nitrobenzene (2.0 g; 7.6 mmol) was dissolved in 35 ml of concentrated hydrochloric acid, followed by the addition of 6.9 g (30.6 mmol; 4.0 equivalents) of tin(II) chloride dihydrate. The resultant mixture was stirred under heating for 1 hour over an oil bath controlled at 100° C. The reaction mixture was allowed to cool down to room temperature and then diluted with water. The resulting mixture was basified with concentrated aqueous ammonia and then extracted twice with ethyl acetate. The extracts were combined, dried over sodium sulfate and then concentrated under reduced pressure. The residue was added with 4N hydrochloric acid/dioxane, followed by concentration. The residue was crystallized from a mixed solvent of a small amount of methanol and ethyl ether, whereby 1.97 g (7.3 mmol) of the title compound were obtained as yellow crystals (yield: 96.1%).

1. temperatureunder heating for 1 hour over an oil bath
2. customcontrolled at 100° C
3. extractionextracted twice with ethyl acetate
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. additionThe residue was added with 4N hydrochloric acid/dioxane
7. concentrationfollowed by concentration
8. customThe residue was crystallized from a mixed solvent of a small amount of methanol and ethyl ether

ORD record

ord-4bc1cbca49534db88727e9a0ee88f477

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05852011