Water → HCID 21440167, compound

HRID 328969Notes

Reaction equation

HRID 328969 reaction equation
S(=O)(=O)(O)[OH:2].N[C:7]1[C:12]2[C:13]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:14][S:15](=[O:17])(=[O:16])[C:11]=2[CH:10]=[C:9]([C:24]([OH:26])=[O:25])[CH:8]=1.N([O-])=O.[Na+].[OH2:31]>>[C:13]([C:12]1[C:11]([S:15](=[O:17])(=[O:16])[NH2:14])=[CH:10][C:9]([C:24]([OH:26])=[O:25])=[CH:8][C:7]=1[OH:2])(=[O:31])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 21440251HCID 21440251, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21440167HCID 21440167, compound

Procedure

To a stirred mixture of conc. sulfuric acid (125 ml) and water (40 ml), 4-amino-6-carboxy-3-phenyl-1,2-benzisothiazole 1,1-dioxide (15.1 g) is added in portions. The resulting solution is cooled to 0° -5° C. and the amine is diazotized by the dropwise addition of a solution of sodium nitrite (3.8 g) in water (40 ml). The diazonium-mixture is then heated on a steam bath for 2-3 hours until the nitrogen evolution has ceased. After cooling and dilution with water (about 200 ml), the resulting precipitate is collected by filtration and washed with water. The material is dried and recrystallized twice from aqueous ethanol. The thus purified material is dissolved in 1 N sodium hydroxide and the solution is added to a slight excess of ice-cold 1 N hydrochloric acid. The resulting precipitate is collected by filtration, washed with water and dried in vacuo in the presence of P2O5 to give 4-benzoyl-3-hydroxy-5-sulfamylbenzoic acid as a hemihydrate.

Workup

  1. additionis added in portions
  2. temperatureThe resulting solution is cooled to 0° -5° C.
  3. temperatureAfter cooling
  4. filtrationdilution with water (about 200 ml), the resulting precipitate is collected by filtration
  5. washwashed with water
  6. customThe material is dried
  7. customrecrystallized twice from aqueous ethanol
  8. dissolutionThe thus purified material is dissolved in 1 N sodium hydroxide
  9. additionthe solution is added to a slight excess of ice-cold 1 N hydrochloric acid
  10. filtrationThe resulting precipitate is collected by filtration
  11. washwashed with water
  12. dry with materialdried in vacuo in the presence of P2O5

Sources & evidence

ORD record
ord-d30a6bf5ca67494d9af79fba1933751c
Source dataset
uspto-grants-1977_04
Patent number
US04018794

Reaction notes

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