Ammonium Hydroxide → 2,3-Dichloro-5-sulfamoylbenzoic acid

HRID 1666565Notes

Reaction equation

HRID 1666565 reaction equation
[Cl:1][C:2]1[C:10]([Cl:11])=[CH:9][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH4+:16].[OH-]>C(Cl)Cl>[NH2:16][S:12]([C:8]1[CH:9]=[C:10]([Cl:11])[C:2]([Cl:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 205061302,3-Dichloro-5-(chlorosulfonyl)benzoic acid

Product 1

HCID 180713352,3-Dichloro-5-sulfamoylbenzoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 20 ml scintillation vial was added 2,3-dichloro-5-(chlorosulfonyl)benzoic acid (170 mg, 0.587 mmol). To this was added 1.5 ml of DCM and 7 ml of 7M NH4OH. The reaction mixture was stirred vigorously at room temperature overnight. After consumption of the starting material, the reaction solution was concentrated to half volume with a rotary evaporator and acidified with 6M HCl to ˜pH 4.5. The resulting solution was left at room temperature until the product precipitated. The product was collected by vacuum filtration and air dried, yielding 5-(aminosulfonyl)-2,3-dichlorobenzoic acid (80 mg, 50%) as light yellow solid.

Workup

  1. customAfter consumption of the starting material
  2. concentrationthe reaction solution was concentrated to half volume with a rotary evaporator
  3. waitThe resulting solution was left at room temperature until the product
  4. customprecipitated
  5. filtrationThe product was collected by vacuum filtration and air
  6. customdried

Sources & evidence

ORD record
ord-520e45455ba1488997336aa2c9e5e5ae
Source dataset
uspto-grants-2011_10
Patent number
US08044075B2

Reaction notes

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