Dimethyl Sulfate → N,N,N-trimethyl-2-[methyl(4-nitrophenyl)-amino]ethanaminium methylsulfate
Reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1.[S:17]([O:22]C)([O:20][CH3:21])(=[O:19])=[O:18]>C(#N)C>[CH3:21][O:20][S:17]([O-:22])(=[O:19])=[O:18].[CH3:1][N+:2]([CH3:21])([CH3:16])[CH2:3][CH2:4][N:5]([CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1Participants
4
Procedure
8.0 g (36 mmol) of the compound from Step 9.1 was dissolved in 50 mL of acetonitrile and to the solution was added dropwise 4.55 g (36 mmol) of dimethyl sulfate over a period of 5 minutes with agitation which caused the reaction mixture to warm up slightly while the product gradually separated in crystalline form. The mixture was allowed to agitate for an additional 3 hours at room temperature after which it was suction-filtered. The filter cake was washed with a small amount of acetonitrile and then dried at 40° C. under vacuum. This gave 11.0 g (88% of the theoretical) of yellow crystals.