N-Methylaniline → N-Methylaniline

HRID 380555Notes

Reaction equation

HRID 380555 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16](Cl)(=[O:18])=[O:17].[OH-].[Na+]>>[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 7515N-MethylanilineHCID 14798Sodium HydroxideHCID 5204032-Bromobenzenesulfonyl chloride

Product 2

HCID 7515N-MethylanilineHCID 7938026HCID 7938026, compound

Procedure

Freshly distilled N-methylaniline (b.p. 196° C.) is prepared. To 1.07 g (0.01 mole) of the N-methylaniline is added 2.56 g (0.01 mole) of 2-bromobenzenesulfonyl chloride (98 w/w %). The mixture is stirred until hot. Ten percent sodium hydroxide is then added dropwise with stirring until the solution is slightly alkaline, and 2-bromo-N-methylbenzenesulfonanilide is formed as a viscous red-brown liquid. It is washed with water several times until the wash water is neutral to litmus paper. A viscous red-brown liquid is extracted with ether, and the ether layer is dried over magnesium sulfate, filtered and the solvent removed by evaporation. The yield of red-brown oil is 2.30 g (70% yield). 1H NMR (deuterioacetone): δ 7.1-8 (m, 9 ArH), 3.3 (s, 3H, N—CH3).

Workup

  1. stirringwith stirring until the solution

Sources & evidence

ORD record
ord-03316b2883f44a89abf035fc38c14394
Source dataset
uspto-grants-2001_10
Patent number
US06303630B1

Reaction notes

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