反应详情

A water cooled stirred suspension of 13.41 g (0.05 mol) of 6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl acetic acid, 50 ml of sieve-dried methylene chloride and three drops of dimethylformamide was treated for a few minutes with 6.54 g (0.055 mol) of thionyl chloride. After total addition the suspension was stirred 15 minutes with cooling and was then intermittently warmed until the evolution of HCl ceased. A stirred ice water chilled solution of 13.37 g (0.15 mol) of 2-amino-2-methyl-1-propanol and 50 ml of sieve-dried methylene chloride was treated dropwise over 0.5 hour with the acid chloride solution. After total addition the resultant suspension was stirred with cooling for 20 minutes and was then stirred 1.5 hours at ambient temperature. The suspension was vacuum filtered and the filtrate was washed with 100 ml each of 5% HCl, water, and 5% Na2CO3. The organic phase was dried by extracting with 500 ml of saturated NaCl solution and then over anhydrous Na2SO4. The resultant mixture was filtered and the filtrate was concentrated to an oil which was dried by azeotropic distillation of absolute ethanol to afford 14.3 g (84.3%) of a crude product. Two recrystallizations from benzene and a final recrystallization from isopropanol afforded 7.0 g (41.2%) of crystals of 6,11-dihydro-N-(1-hydroxy-2-methyl-2-propyl)-11-oxodibenz[b,e]oxepin-2-yl acetamide, m.p. 132°-134° C.

1. additionAfter total addition the suspension
2. stirringwas stirred 15 minutes
3. temperaturewith cooling
4. stirringwas stirred
5. temperaturewith cooling for 20 minutes
6. stirringwas then stirred 1.5 hours at ambient temperature
7. filtrationfiltered
8. washthe filtrate was washed with 100 ml each of 5% HCl, water, and 5% Na2CO3
9. customThe organic phase was dried
10. extractionby extracting with 500 ml of saturated NaCl solution
11. filtrationThe resultant mixture was filtered
12. concentrationthe filtrate was concentrated to an oil which
13. dry with materialwas dried by azeotropic distillation of absolute ethanol
14. customto afford 14.3 g (84.3%) of a crude product
15. customTwo recrystallizations from benzene
16. customa final recrystallization from isopropanol