N-Methylaniline → HCID 4806097, compound

HRID 380556Notes

Reaction equation

HRID 380556 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[S:16](Cl)(=[O:18])=[O:17].[OH-].[Na+]>>[Cl: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

4

Reactant 3

HCID 7515N-MethylanilineHCID 14798Sodium HydroxideHCID 761872-Chlorobenzenesulfonyl chloride

Product 1

HCID 4806097HCID 4806097, compoundYield 87%

Procedure

To 0.97 g (˜0.01 mole) of freshly prepared N-methyl-aniline (b.p. 196° C.) is added 1.94 g (˜0.01 mole) of 2-chlorobenzenesulfonyl chloride (98 w/w %). The mixture is stirred until it becomes hot, and then ten percent sodium hydroxide is added dropwise with stirring until the solution is slightly alkaline. 2-chloro-N-methylbenzenesulfonanilide is formed as a viscous yellow liquid. It is washed with water several times until the wash water is neutral to litmus paper, and the viscous yellow liquid extracted with ether. The ether layer is dried over magnesium sulfate, filtered and the solvent removed by evaporation. The yield of a yellow oil is 2.2 g (87% yield).

Workup

  1. stirringwith stirring until the solution

Sources & evidence

ORD record
ord-d0548a53f8314a2aab34cd0c63beeeab
Source dataset
uspto-grants-2001_10
Patent number
US06303630B1

Reaction notes

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