Dimethyl Sulfoxide → Cyclohexane, azido-

Temperature

75 °C

Cyclohexyl bromide (2.74 mL, 0.023 mol) was added to a stirred solution of 0.5M sodium azide in DMSO (50 mL, 0.025 mol) at room temperature, under an atmosphere of nitrogen. The reaction mixture was heated to 75° C. behind a blast shield and stirred for 5 h. The reaction mixture was then cooled with an ice-bath, quenched by the addition of water (75 mL) and extracted with diethyl ether (3×125 mL). The combined organic layers were washed with brine (75 mL), dried (MgSO4), filtered and concentrated in vacuo to afford the title compound as a crude oil (2.4 g) which was used without further purification.

1. temperatureThe reaction mixture was then cooled with an ice-bath
2. customquenched by the addition of water (75 mL)
3. extractionextracted with diethyl ether (3×125 mL)
4. washThe combined organic layers were washed with brine (75 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-47bc8e8ab3894df38d504e2b25ea6168

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211894B2