N-[2-(4-nitroanilino)ethyl]methanesulfonamide → N-methyl-N-[2-(4-nitrophenylamino)ethyl]methanesulfonamide
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].S([O-])(O[CH3:22])(=O)=O>[OH-].[Na+]>[CH3:22][N:13]([CH2:12][CH2:11][NH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[S:14]([CH3:17])(=[O:16])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 30 °C
Procedure
25.9 g (0.1 mol) of N-[2-(4-nitrophenylamino)ethyl]methanesulfonamide (22) were dissolved in 200 mL of 1N sodium hydroxide at 50° C. The insoluble matter was filtered off, the filtrate was cooled to 30° C. and 11.4 mL (0.12 mol) of methyl sulfate were added dropwise. The mixture was stirred for 1 hour at room temperature and then heated to 40° C. and the yellow precipitate was filtered off. The product was reslurried in 0.5N sodium hydroxide and in water. The wet crude product was recrystallized from 50 mL of 96% ethanol with carbon black. 13.3 g of product with a melting point of 109° C. were isolated.
Workup
- filtrationThe insoluble matter was filtered off
- temperatureheated to 40° C.
- filtrationthe yellow precipitate was filtered off
- customThe wet crude product was recrystallized from 50 mL of 96% ethanol with carbon black
Sources & evidence
- ORD record
- ord-bc3cf21ee81648e88a9a555567bdddee
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07347879B2
Reaction notes
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