Hydrochloric Acid → 5-[(2-Chloroethyl)amino]-2-benzofuran-1(3H)-one

Temperature

60 °C

To a suspension of 2-chloro-N-(1-oxo-1,3-dihydroisobenzofuran-5-yl)-acetamide (1.0 g, 4.43 mmol) in THF (15 ml) was added 2M borane-methyl sulfide complex solution in THF (6.6 ml, 13.2 mmol) under nitrogen. After stirred at 60° C. under nitrogen for 2 hours, the resulting mixture was cooled in an ice bath, followed by the addition of aqueous HCl solution. The mixture was stirred at room temperature for 20 minutes, then heated at 60° C. for 40 minutes. After cooled to room temperature, the mixture was basified with aqueous NaOH solution, and then it was partitioned between water (50 ml) and CHCl3 (50 ml). The aqueous layer was extracted with CHCl3 (2×50 ml). The combined organic layers were washed with water, dried over anhydrous Na2SO4 Removal of the solvent led to a crude product. Trituration of the crude product with MeOH gave 5-(2-chloro-ethylamino)-3H-isobenzofuran-1-one as a light brown solid (0.4 g, 42%).

1. temperaturethe resulting mixture was cooled in an ice bath
2. stirringThe mixture was stirred at room temperature for 20 minutes
3. temperatureheated at 60° C. for 40 minutes
4. temperatureAfter cooled to room temperature
5. customit was partitioned between water (50 ml) and CHCl3 (50 ml)
6. extractionThe aqueous layer was extracted with CHCl3 (2×50 ml)
7. washThe combined organic layers were washed with water
8. dry with materialdried over anhydrous Na2SO4 Removal of the solvent

ORD record

ord-e1fff3b6b23644b3a907610927e25527

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07060844B2