Iodine chloride → HCID 490382, compound

Iodine monochloride (92 mg, 0.56 mmol) was added slowly during a five minute period to a suspension of sodium azide (129 mg, 2.0 mmol) in dry acetonitrile (10 ml) at ice-bath temperature with stirring. This mixture was stirred for a further 5 min., a solution of 1 (105 mg, 0.49 mmol) in dry acetonitrile (15 ml) was added, the reaction mixture was stirred at 0° C. for 30 min. The resulting red-brown colored reaction mixture was poured onto ice cold water (25 ml), the mixture was extracted with ethyl acetate (3×50 ml) and the ethyl acetate extract was washed with 5% aqueous sodium thiosulfate (50 ml). Drying the colorless ethyl acetate fraction (Na2SO4), removal of the solvent in vacuo and purification of the residue obtained by elution from a silica gel column using chloroform:methanol (93:7, v/v) as eluent afforded 2c (65 mg, 34%) as a viscous oil.

1. stirringThis mixture was stirred for a further 5 min.
2. stirringthe reaction mixture was stirred at 0° C. for 30 min
3. additionThe resulting red-brown colored reaction mixture was poured onto ice cold water (25 ml)
4. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
5. extractionthe ethyl acetate extract
6. washwas washed with 5% aqueous sodium thiosulfate (50 ml)
7. customDrying
8. customthe colorless ethyl acetate fraction (Na2SO4), removal of the solvent
9. customin vacuo and purification of the residue
10. customobtained by elution from a silica gel column

ORD record

ord-c7b83534f2384d4580788ad7ebb35d8b

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08227594B2