反应详情

A solution of [5-(4-Chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-yl]methyl methanesulfonate (58 g, 0.134 mol) in THF (200 mL) and NH4OH aq. (25%, 412 mL, 2.68 mol) was stirred at room temperature for 15 hours. The excess ammonia was removed in vacuo and EtOAc (200 mL) and sat. aq. NaHCO3 (150 mL) was added. The organic layer was separated and the aqueous phase was extracted with EtOAc, the combined organic layers were washed with sat. aq. NaHCO3 (2×150 mL), brine (200 mL) and water (1×200 mL), dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to afford the crude material (89.85 g). This material was purified by column chromatography using dichloromethane, methanol and ammonium hydroxide (97:3:1) in silica gel to yield the [5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4,5-dihydro-1H-pyrazole-3-yl]methyl amine (18.90 g, 40%, two steps) as a yellow solid.

1. customThe excess ammonia was removed in vacuo and EtOAc (200 mL) and sat. aq. NaHCO3 (150 mL)
2. additionwas added
3. customThe organic layer was separated
4. extractionthe aqueous phase was extracted with EtOAc
5. washthe combined organic layers were washed with sat. aq. NaHCO3 (2×150 mL), brine (200 mL) and water (1×200 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customto afford the crude material (89.85 g)
9. customThis material was purified by column chromatography