반응 #4086
ord-34a0944dc3144a9f9ca25f89152134d8
반응 조건
후처리
- 1workup.ADDITIONAt the end of addition the reaction mixture
- 2workup.STIRRINGwas stirred at room temperature for 2 hours
- 3온도heated to 75°-78° C. for 16 hours
- 4기타The reaction mixture was partitioned between methylene chloride (300 ml) and water (250 ml)
- 5기타The aqueous phase was separated
- 6추출extracted twice with methylene chloride (150 ml)
- 7세척The combined organic solution was washed twice with water, twice with HCl (2N, 100 ml), brine (2×50 ml)
- 8건조dried over Na2SO4
- 9농축concentrated to about 50 ml
- 10workup.ADDITIONEther (50 ml) was added
- 11기타The product was crystallized out
- 12workup.WAITupon standing overnight
- 13기타(about 16 hours)
- 14기타Recrystallization from methylene chloride and ether
실험 절차
A slurry was prepared comprising 5-chloroindoline (15.3 gm, 0.1 mole), dimethylsulfoxide (DMSO) [50 ml] and sodium hydride (5.28 gm, 50% in oil, washed with hexane). The slurry was permitted to stir at room temperature for 1 hour. To this a solution of o-fluorobenzamide (15.2 gm, 1.1 eq.) in DMSO (20 ml) was added dropwise with the temperature between 17°-19° C. At the end of addition the reaction mixture was stirred at room temperature for 2 hours, then heated to 75°-78° C. for 16 hours. The reaction mixture was partitioned between methylene chloride (300 ml) and water (250 ml). The aqueous phase was separated and extracted twice with methylene chloride (150 ml). The combined organic solution was washed twice with water, twice with HCl (2N, 100 ml), brine (2×50 ml), dried over Na2SO4, concentrated to about 50 ml. Ether (50 ml) was added. The product was crystallized out upon standing overnight (about 16 hours). The yield was 14.2 gm (52%); m.p. 137°-138° C. Recrystallization from methylene chloride and ether yielded 2-(5-chloro-indolin-1-yl)benzamide (11.82 gm) m.p. 137°-138° C.