3-Chloro-N-(3-chloropropyl)-4-methylaniline synthesis
- Product Name:3-Chloro-N-(3-chloropropyl)-4-methylaniline
- CAS Number:333985-68-5
- Molecular formula:C10H13Cl2N
- Molecular Weight:218.12
Yield:333985-68-5 86%
Reaction Conditions:
with triethylamine;potassium iodide in N,N-dimethyl-formamide at 20; for 72 h;
Steps:
1.1
Step 1: 3-chloro-N-(3-chloropropyl)-4-methylaniline To a solution of 3-chloro-4-methylaniline (14.16 g, 100 mmol) in DMF (N,N-dimethyl formamide) (10 mL), were added 1-bromo-3-chloropropane (30.5 mL, 300 mmol), potassium iodide (1.66 g, 10 mmol) and triethylamine (60 mL). The mixture was stirred for 3 days at room temperature, then distilled off the solvents with a low boiling point, diluted with ethyl ether, and washed by a saturated saline. The separated organic phase was dried with sodium sulfate and concentrated under reduced pressure. The concentrate was separated through column chromatography (petroleum ether/ethyl acetate=25/1, v/v) to obtain compound 1 as light brown oil (18.64 g, yield: 86%). 1HNMR (CDCl3, 300 MHz) δ: 7.01-6.98 (d, 1H, J=8.1 Hz), 6.64-6.63 (d, 1H, J=2.4 Hz), 6.46-6.42 (dd, 1H, J=2.4 Hz, 5.7 Hz), 3.66-3.62 (t, 2H, J=6.3 Hz), 3.31-3.27 (t, 2H, J=6.6 Hz), 2.45 (s, 3H), 2.09-2.01 (m, 2H).
References:
US2011/251192,2011,A1 Location in patent:Page/Page column 5
