Caprolactam → HCID 86749896, compound

Temperature

101 °C

To a 1000 mL three-necked round-bottomed flask equipped with a reflux condenser, internal thermometer, argon inlet, and mechanical stirrer, are added ε-caprolactam (48.04 g, 0.42 mol), toluene (340 mL), and triethylamine (189.00 g, 1.87 mol). The mixture is heated to reflux (ca. 101° C.) for 15 min. While at that temperature, acid chloride 3 (100.00 g, 0.47 mol) is added as a solid over 30 min. The reaction is maintained at reflux for an additional 1.75 h before the heat is removed. At room temperature, the mixture is filtered and the salts washed with toluene. The dark filtrate is washed with saturated sodium bicarbonate solution (3×250 mL), water (100 mL), and dried over MgSO4. The mixture is filtered and concentrated by rotary evaporation at about 50° C. (water aspirator) and then by Kugelrohr distillation at 60° C. for 1 h to give 89.64 g (83%) of 4 as a dark red oil.

1. customTo a 1000 mL three-necked round-bottomed flask equipped with a reflux condenser
2. temperatureThe mixture is heated
3. temperatureThe reaction is maintained
4. temperatureat reflux for an additional 1.75 h before the heat
5. customis removed
6. filtrationAt room temperature, the mixture is filtered
7. washthe salts washed with toluene
8. washThe dark filtrate is washed with saturated sodium bicarbonate solution (3×250 mL), water (100 mL)
9. dry with materialdried over MgSO4
10. filtrationThe mixture is filtered
11. concentrationconcentrated by rotary evaporation at about 50° C. (water aspirator)
12. distillationby Kugelrohr distillation at 60° C. for 1 h

ORD record

ord-eade527514dd4c81b81b1b5c0254588f

Source dataset

uspto-grants-1997_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05599781