Diethyl Ether → N-cyano-N-methyl-3-toluidine
Reaction equation
[N:1]#[C:2]Br.[CH3:4][NH:5][C:6]1[CH:11]=CC=[C:8]([CH3:12])[CH:7]=1.C(Cl)Cl.C(O[CH2:19][CH3:20])C>>[C:2]([N:5]([CH3:4])[C:6]1[CH:7]=[CH:8][CH:12]=[C:19]([CH3:20])[CH:11]=1)#[N:1]Participants
5
Procedure
A solution of cyanogen bromide (1.59 g, 15 mmol) in diethylether (10 ml) was added dropwise to a stirred solution of N-methyl-3-toluidine (2.91 g, 24 mmol) in diethylether (90 ml) at 0° C. After the addition, the reaction mixture was stirred at room temperature for 14 h. A solution with white precipitates was formed and the precipitates were removed by filtration. The etherate solution was further washed with aqueous HCl (1N, 20 ml, three times) as well as brine (10 ml), dried over MgSO4, filtered, and concentrated. The product was obtained as a yellow liquid in 70% yield. IR (CH2Cl2): 2240 cm−1.
Workup
- additionAfter the addition
- customA solution with white precipitates
- customwas formed
- customthe precipitates were removed by filtration
- washThe etherate solution was further washed with aqueous HCl (1N, 20 ml, three times) as well as brine (10 ml)
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customThe product was obtained as a yellow liquid in 70% yield
Sources & evidence
- ORD record
- ord-b35b67d9ee52457d8e47d0fd24bb386c
- Source dataset
- uspto-grants-2001_06
- Patent number
- US06251948B1
Reaction notes
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