Water → N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamide

HRID 1050981Notes

Reaction equation

HRID 1050981 reaction equation
S(=O)(=O)(O)O.O.[CH3:7][N:8]([CH3:26])[S:9]([C:12]1[C:20]2[O:19]C(C(C)(C)C)=[N:17][C:16]=2[CH:15]=[CH:14][C:13]=1[Cl:25])(=[O:11])=[O:10]>O1CCOCC1>[NH2:17][C:16]1[C:20]([OH:19])=[C:12]([S:9]([N:8]([CH3:7])[CH3:26])(=[O:10])=[O:11])[C:13]([Cl:25])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 671285552-Tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide

Product 1

HCID 23447758N,N-Dimethyl-3-amino-6-chloro-2-hydroxybenzenesulfonamideYield 96.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

11 ml (205 mmol; 1.20 V) of sulfuric acid and 11 ml of water were added dropwise to a solution of 9.12 g (28.8 mmol; 1.0 eq) of 2-tert-butyl-6-chlorobenzooxazole-7-sulfonic acid dimethylamide in 41 ml of 1,4-dioxane. The reaction medium was refluxed for six and a half hours. The reaction medium was concentrated and 440 ml of 1 N sodium hydroxide were added (pH at 8). The solution was extracted with ethyl acetate. The organic phases were combined, dried over magnesium sulfate, filtered and evaporated. 6.94 g of 3-amino-6-chloro-2-hydroxy-N,N-dimethylbenzenesulfonamide were obtained in the form of a brown solid. Yield=96%.

Workup

  1. temperatureThe reaction medium was refluxed for six and a half hours
  2. concentrationThe reaction medium was concentrated
  3. addition440 ml of 1 N sodium hydroxide were added (pH at 8)
  4. extractionThe solution was extracted with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-bee358e217c84d59a3241c41db5ff317
Source dataset
uspto-grants-2016_07
Patent number
US09388149B2

Reaction notes

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