Ethyl 2-(4-aminosulfonylphenyl)thiazole-4-carboxylate → 2-(p-Sulfamoylphenyl)thiazole-4-carboxylic acid

HRID 460178Notes

Reaction equation

HRID 460178 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:16]([O:18]CC)=[O:17])[N:15]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO.O>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:16]([OH:18])=[O:17])[N:15]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 18771776Ethyl 2-(4-aminosulfonylphenyl)thiazole-4-carboxylate

Product 1

HCID 187720852-(p-Sulfamoylphenyl)thiazole-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

In an oven-dried, 100-mL, round-bottomed flask was placed ethyl 2-(4-aminosulfonylphenyl)thiazole-4-carboxylate (1300 mg, 4.2 mmol), LiOH monohydrate (350 mg, 8.3 mmol) in MeOH (40 mL) and H2O (4 mL). The solution was heated to 75° C. for 3 h, cooled to RT, and concentrated. The resulted yellow solid was dissolved in H2O (10 mL), extracted with EtOAc (1×15 mL). The aqueous layer was acidified with 2N aqueous HCl (4.15 mL). The precipitate was filtered, and washed with H2O (10 mL) to afford the title compound as a light-yellow solid. MS m/z: 285 (M+H).

Workup

  1. temperaturecooled to RT
  2. concentrationconcentrated
  3. dissolutionThe resulted yellow solid was dissolved in H2O (10 mL)
  4. extractionextracted with EtOAc (1×15 mL)
  5. filtrationThe precipitate was filtered
  6. washwashed with H2O (10 mL)

Sources & evidence

ORD record
ord-3abc1e73b0024a69ab2d287258bf2033
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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