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 heat for 1 hour over an oil bath controlled at 100° C. The reaction mixture was allowed to cool down to room temperature, followed by dilution with water. The diluted solution was basified with concentrated aqueous ammonia and then extracted twice with ethyl acetate. The extract was dried over sodium sulfate and then concentrated under reduced pressure. The residue so obtained was added with 4N hydrochloric acid/dioxane and concentrated. The concentrate was then crystallized from a small amount of methanol/ether, whereby 1.97 g (7.3 mmol) of the title compound were obtained as yellow crystals (yield: 96.1%).

1. temperatureunder heat for 1 hour over an oil bath
2. customcontrolled at 100° C
3. extractionextracted twice with ethyl acetate
4. dry with materialThe extract was dried over sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue so obtained
7. concentrationconcentrated
8. customThe concentrate was then crystallized from a small amount of methanol/ether

ORD record

ord-8e51c7e470e24bd18e4465f3228bec2f

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05852011