Ammonium Hydroxide → 3,5-Dichloro-2-hydroxybenzenesulfonamide

HRID 637522Notes

Reaction equation

HRID 637522 reaction equation
[OH:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].[NH4+:14].[OH-]>C(Cl)Cl>[OH:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[CH:4][C:3]=1[S:10]([NH2:14])(=[O:12])=[O:11]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 900783,5-Dichloro-2-hydroxybenzenesulphonyl chloride

Product 1

HCID 2947193,5-Dichloro-2-hydroxybenzenesulfonamideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 39.16 g of the product from Example 3 in 100 ml CH2Cl2 was contacted with 250 ml of 28% NH4OH at 5°-8° C. Following removal of CH2Cl2 by a N2 sparge the mixture was acidified to pH 3. Filtration afforded 42.7 g of 61% pure 2-hydroxy-3,5-dichlorobenzenesulfonamide (D) (71% yield).

Workup

  1. customremoval of CH2Cl2 by a N2
  2. customsparge the mixture
  3. filtrationFiltration

Sources & evidence

ORD record
ord-e11429a466cf4698accf16afd6405a68
Source dataset
uspto-grants-1985_12
Patent number
US04556733

Reaction notes

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