Ammonium Hydroxide → (+/-)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamide
반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25](=[O:27])[CH3:26])[CH:20]=[C:21]([Cl:23])[CH:22]=1.[NH4+].[OH-]>>[Cl:16][C:17]1[CH:18]=[C:19]([NH:24][C:25](=[O:27])[CH3:26])[CH:20]=[C:21]([Cl:23])[C:22]=1[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1참가 물질
4
반응 조건
- 온도
- 100 °C
실험 절차
α-(4-chlorophenyl)-4-pyridinemethanol (0.0512 mol), N-(3,5-dichlorophenyl)-acetamide (0.102 mol) and polyphosphoric acid (210 g) were stirred at 140° C. for 90 minutes. The mixture was cooled to 100° C., poured out into ice water, basified with NH4OH and extracted with CH2Cl2. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was taken up in 2-propanone and diethyl ether. The precipitate was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97.5/2.5/0.1). The pure fraction was collected and the solvent was evaporated, yielding 17.94 g (87%) of (±)-N-[3,5-dichloro-4-[(4-chlorophenyl)-4-pyridinylmethyl]phenyl]-acetamide (interm. 28).