N-[5-(3,5-Dichloro-4-sulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide → 4-(2-Amino-4-methyl-thiazol-5-yl)-2,6-dichloro-benzenesulfonamide

HRID 1092944Notes

Reaction equation

HRID 1092944 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[S:17][C:16]([NH:18]C(=O)C)=[N:15][C:14]=2[CH3:22])[CH:5]=[C:6]([Cl:12])[C:7]=1[S:8](=[O:11])(=[O:10])[NH2:9]>Cl.C(O)C>[NH2:18][C:16]1[S:17][C:13]([C:4]2[CH:5]=[C:6]([Cl:12])[C:7]([S:8]([NH2:9])(=[O:10])=[O:11])=[C:2]([Cl:1])[CH:3]=2)=[C:14]([CH3:22])[N:15]=1

Participants

4

Reactant 1

HCID 86598402N-[5-(3,5-Dichloro-4-sulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide

Product 1

HCID 858616664-(2-Amino-4-methyl-thiazol-5-yl)-2,6-dichloro-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A solution of N-[5-(3,5-dichloro-4-sulfamoyl-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 6) (0.70 g, 1.84 mmol) in aqueous hydrochloric acid (5M, 10 ml) and ethanol (20 ml) is heated at reflux for 90 minutes. When cool, the mixture is concentrated to remove ethanol and the aqueous solution is brought to pH 9 by addition of aqueous sodium hydroxide (4M). The product is extracted with n-butanol (50 ml) and the organic extract is dried over MgSO4. Removal of the solvent followed by chromatography on silica (eluting with ethyl acetate-hexane, 2:1 increasing to 4:1) affords the title compd. MH+ (MS, AP+): 337.8, 339.5

Workup

  1. temperatureat reflux for 90 minutes
  2. temperatureWhen cool
  3. concentrationthe mixture is concentrated
  4. customto remove ethanol
  5. additionthe aqueous solution is brought to pH 9 by addition of aqueous sodium hydroxide (4M)
  6. extractionThe product is extracted with n-butanol (50 ml)
  7. extractionthe organic extract
  8. dry with materialis dried over MgSO4
  9. customRemoval of the solvent
  10. customaffords the title

Sources & evidence

ORD record
ord-059f50e3ca1740f09aadcf1c9c122f6b
Source dataset
uspto-grants-2012_03
Patent number
US08129541B2

Reaction notes

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