Aniline, N,N-bis(2-chloroethyl)-m-nitro- → HCID 22096854, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:9]=[C:10]([N+:14]([O-])=O)[CH:11]=[CH:12][CH:13]=1)[CH2:5][CH2:6][Cl:7].O.N>Cl.O>[ClH:1].[Cl:1][CH2:2][CH2:3][N:4]([CH2:5][CH2:6][Cl:7])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
In 35 ml of concentrated hydrochloric acid was dissolved 2.0 g (7.6 mmols) of 3-[N,N-bis(2-chloroethyl)amino]nitrobenzene, and 6.9 g (30.6 mmols, 4.0 eq.) of stannic chloride (II) dihydrate was added, followed by stirring for 1 hour in an oil bath at 100° C. Next, the solution was allowed to stand until its temperature lowered to room temperature, and then diluted with water. The solution was basified with concentrated ammonia water, extracted with ethyl acetate twice, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. Afterward, 4N hydrochloric acid and dioxane were added to the resulting residue, and after concentration, the residue was crystallized from a small amount of methanol-ether to obtain 1.97 g (7.3 mmols, 96.1%) of the desired compound in the state of yellow crystals.
Workup
- additionwas added
- customlowered to room temperature
- extractionextracted with ethyl acetate twice
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- additionAfterward, 4N hydrochloric acid and dioxane were added to the resulting residue
- concentrationafter concentration
- customthe residue was crystallized from a small amount of methanol-ether
Sources & evidence
- ORD record
- ord-7f95ec6f1908402e9f97561588d3b7d0
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05821258
Reaction notes
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