Hydrochloric Acid → 1-Azido-2-chlorobenzene

Temperature

0 °C

2-Chlorophenylhydrazine hydrochloride (1.0 g) suspended in 6.0 ml of diethyl ether was dropped into 5 ml of concentrated hydrochloric acid cooled at 0° C. After the reaction solution was stirred for 10 minutes, 462 mg of sodium nitrite dissolved in 2.0 ml of water was dropped into the reaction solution and the mixture was stirred for 2 hours together with raising the temperature up to room temperature. Water was added to the reaction solution, the mixture was extracted with ethyl acetate and the ethyl acetate layer washed with a saturated aqueous saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo to give 506 mg of the title compound as a red oily crude product.

1. additionwas dropped into the reaction solution
2. stirringthe mixture was stirred for 2 hours together
3. temperaturewith raising the temperature up to room temperature
4. extractionthe mixture was extracted with ethyl acetate
5. washthe ethyl acetate layer washed with a saturated aqueous saline solution
6. dry with materialdried over sodium sulfate
7. customThe solvent was evaporated in vacuo

ORD record

ord-b37e6e88d3cf497781369017a98275b6

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07858800B2