N-(联苯-2-基)-2-氯乙酰胺

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: AlCl3 (12.1 g) was added to a solution of N-biphenyl-2-yl-2-chloro-acetamide (9.9 g) in 1,3-dichlorobenzene (99 mL). The reaction mixture was stirred for 24 hours at 170° C., cooled to 0° C. and poured into ice-water (1500 mL). The suspension obtained was filtered off, the precipitate washed with water (250 mL), 2 portions of hexane/dichloromethane 4:1 (25 mL), 2 portions of water (125 mL) and 2 portions of hexane (25 mL) affording 5H,7H-dibenzo[b,d]azepin-6-one (6.9 g, 82.5%) as an off-white powder. cooled to 0° C. The suspension obtained was filtered off the precipitate washed with water (250 mL), 2 portions of hexane/dichloromethane 4:1 (25 mL), 2 portions of water (125 mL) and 2 portions of hexane (25 mL)

反应条件: temp:-18.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Triethylamine (26.7 g) was added to a solution of 2-aminobiphenyl (41.4 g) in dichloromethane (248 mL) at room temperature. The solution obtained was cooled to −18° C. and chloracetylchloride (28.8 g) was slowly added. The suspension obtained was further stirred for 1 hour at 0° C. and for 15 hours at room temperature. Dichloromethane (150 mL), ice-water (500 mL), water (500 mL) and saturated aqueous NaHCO3 (150 mL) were added. After stirring, the phases were separated, the organic phase was washed with half-saturated aqueous NaCl (1000 mL) and the aqueous phases were extracted with dichloromethane (250 mL). The combined organic layers were dried (MgSO4) and concentrated under vacuum to a weight of ca. 100 g. After 40 minutes stirring at room temperature, the precipitate was filtered off, washed with dichloromethane (80 mL) and dried under high vacuum to afford N-biphenyl-2-yl-2-chloro-acetamide (8.6 g, 14.5%) as white crystals. The filtrate was further concentrated under reduced pressure to a weight of ca. 115 g and hexane (100 mL) was added dropwise. After 1 hour of stirring at room temperature, the precipitate was filtered off, washed with 3 portions of hexane/dichloromethane 4:1 (22 mL) and dried under high vacuum affording N-biphenyl-2-yl-2-chloro-acetamide (31.2 g, 53.0%) as a grey powder. The filtrate was concentrated under reduced pressure to a weight of ca. 90 g and stirred for 1 hour at room temperature. The precipitate was filtered off, washed with 2 portions of hexane/dichloromethane 4:1 (17 mL) and dried under high vacuum affording N-biphenyl-2-yl-2-chloro-acetamide (10.8 g, 18.3%) as a grey powder. The solution obtained The suspension obtained After stirring the phases were separated the organic phase was washed with half-saturated aqueous NaCl (1000 mL) the aqueous phases were extracted with dichloromethane (250 mL) The combined organic layers were dried (MgSO4) concentrated under vacuum to a weight of ca. 100 g After 40 minutes stirring at room temperature the precipitate was filtered off washed with dichloromethane (80 mL) dried under high vacuum