Toluene → HCID 67954048, compound

Temperature

45 °C

8-benzyloxy-1-methyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (33.4 g, 113 mmol), tetrabutyl ammonium bromide (7.28 g, 22.6 mmol) and an aqueous solution of 25% sodium hydroxide (20.8 g, 130 mmol) were added to the mixture of toluene (167 mL) and water (150 mL). Ethyl iodide (10.4 mL, 130 mmol) was added thereto, and the reaction was performed at 80° C. for 4 hours. The reaction solution was cooled, and ethyl acetate (334 mL) extraction was performed. The resulting organic layer was washed with water, and the solvent was distilled off under reduced pressure. Ethyl acetate (70 mL) was added to the resulting residue, and the mixture was heated and dissolved. Thereafter, hexane (35 mL) was added thereto, and heating was performed again. The mixture was stirred at 40-50° C. for 30 minutes, and stirred under ice cooling for 1 hour to collect precipitated crystals by filtration. The resulting crystals were washed with ethyl acetate-hexane (1:1; 50 mL), and dried at 60° C., thereby obtaining 39.6 g of a light-yellow, powdery target compound (containing ammonium salt).

1. temperatureThe reaction solution was cooled
2. extractionethyl acetate (334 mL) extraction
3. washThe resulting organic layer was washed with water
4. distillationthe solvent was distilled off under reduced pressure
5. additionEthyl acetate (70 mL) was added to the resulting residue
6. temperaturethe mixture was heated
7. dissolutiondissolved
8. additionThereafter, hexane (35 mL) was added
9. temperatureheating
10. stirringstirred under ice cooling for 1 hour
11. customto collect
12. customprecipitated crystals
13. filtrationby filtration
14. washThe resulting crystals were washed with ethyl acetate-hexane (1:1; 50 mL)
15. customdried at 60° C.
16. customobtaining 39.6 g of a light-yellow,

ORD record

ord-9194b4817d8446de83270bf8d8cd1809

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796447B2