Dimethylformamide → HCID 12069418, compound

Temperature

0 °C

To a suspension of sodium thiomethoxide (1.47 g) in anhydrous tetrahydrofuran (50 ml) was added dropwise a solution of N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (6.0 g) in anhydrous tetrahydrofuran (120 ml) while cooling at 0° C. The resulting mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. At the end of this time anhydrous DMF (30 ml) was added and the resulting mixture stirred at room temperature for 1 hour. DMF (20 ml) was added and then sodium thiomethoxide (0.73 g) and further DMF (50 ml) were added. The resulting mixture was stirred at room temperature for 7 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous sodium hydrogencarbonate solution. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated to afford the desired compound (6.15 g).

1. stirringthe resulting mixture stirred at room temperature for 1 hour
2. stirringThe resulting mixture was stirred at room temperature for 7 hours
3. concentrationThe reaction mixture was concentrated in vacuo
4. customthe residue was partitioned between ethyl acetate and aqueous sodium hydrogencarbonate solution
5. washThe extract was washed with saturated aqueous sodium chloride solution
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated

ORD record

ord-3e5b98bae39f4f348f2714b97d4633c6

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06569877B2