Sodium Chloride → HCID 178515941, compound

Temperature

0 °C

Into the flask, 100 mL of anhydrous toluene and diethyl aluminum chloride (40 mmol, 1.8 M toluene solution) were put and cooled to 0° C. Sodium azide (2.6 g, 40 mmol) was put into the mixture, and the mixture was agitated at room temperature for 4 hours. After the agitated solution was cooled to 0° C. again, 2-hydroxybenzonitrile (20 mmol, 2.38 g) was added thereto. The reaction mixture was refluxed at 80 for 1 day. After the reaction was finished, the mixture was cooled to 0° C., 70 mL of 6 M HCL, 50 mL of distilled water, 100 mL of ethyl acetate, and 80 mL of saturated NaCl were dropped thereon, treated, and extracted. The organic phase was reextracted by using 200 mL of water twice. The combined water layers were extracted with 200 mL of ethyl acetate twice. The combined organic layers were dried through Na2SO4. The solvent was removed to obtain the product. The product was recrystallized from ethyl acetate to obtain a pure product (yield 80%).

1. temperatureAfter the agitated solution was cooled to 0° C. again
2. temperatureThe reaction mixture was refluxed at 80 for 1 day
3. temperaturethe mixture was cooled to 0° C.
4. additiontreated
5. extractionextracted
6. extractionThe combined water layers were extracted with 200 mL of ethyl acetate twice
7. dry with materialThe combined organic layers were dried through Na2SO4
8. customThe solvent was removed
9. customto obtain the product
10. customThe product was recrystallized from ethyl acetate

ORD record

ord-b885536ec01b41a5adf8f4c6e0239067

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431660B2