Sodium Hydroxide → HCID 18365394, compound

HRID 1107706Notes

Reaction equation

HRID 1107706 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17](Cl)(=[O:19])=[O:18].[OH-].[Na+]>>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([N:6]([CH3:7])[C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)(=[O:19])=[O:18]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 702724-Chloro-N-methylbenzenamineHCID 5204032-Bromobenzenesulfonyl chloride

Product 1

HCID 18365394HCID 18365394, compoundYield 69%

Procedure

To 2.51 g (~0.017 mole) of freshly distilled 4-chloro-N-methylaniline (b.p. 102-103° C.) is added 4.26 g (~0.017 mole) of 2-bromo-benzenesulfonyl chloride (98 w/w %). The mixture is stirred until hot. Ten percent sodium hydroxide is added dropwise with stirring until the solution is slightly alkaline. The 2-bromo-4'-chloro-N-methylbenzene-sulfonanilide is formed as viscous liquid. It is washed with water several times until the wash water is neutral. The compound is dried overnight at room temperature. The yield is 4.2 g (69% yield). 1H NMR (deuterioacetone): δ6.8-7.9 (m, 8 ArH), 3.2 (s, 3H, N--CH3).

Workup

  1. stirringwith stirring until the solution

Sources & evidence

ORD record
ord-9d4678010738441a983fa4aff3713551
Source dataset
uspto-grants-2000_05
Patent number
US06063790

Reaction notes

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