Hydrochloric Acid → 4-amino-3-methyl-N-(thiazol-2-yl)benzenesulfonamide

HRID 1876730Notes

Reaction equation

HRID 1876730 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:20])(=[O:19])[NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)=[CH:8][C:7]=1[CH3:21])=O.[OH-].[Na+].Cl>O>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:13][C:14]2[S:15][CH:16]=[CH:17][N:18]=2)(=[O:20])=[O:19])=[CH:8][C:7]=1[CH3:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 594656702,2,2-trifluoro-N-(2-methyl-4-(N-thiazol-2-ylsulfamoyl)phenyl)acetamide

Product 1

HCID 594660994-amino-3-methyl-N-(thiazol-2-yl)benzenesulfonamideYield 31.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Synthesized according to general procedure 71. A solution of 2,2,2-trifluoro-N-(2-methyl-4-(N-thiazol-2-ylsulfamoyl)phenyl)acetamide (1 g, 2.74 mmol), NaOH (1.09 g, 27.4 mmol), and H2O (5 mL) was stirred at RT for 1 h, then cooled to 0° C. 1 N hydrochloric acid (27.4 mL, 27.4 mmol) was added, and the reaction was stirred at 0° C. for 20 min. The formed precipitate was filtered off and dried under vacuum to give 4-amino-3-methyl-N-(thiazol-2-yl)benzenesulfonamide (232 mg, 31%).

Workup

  1. customSynthesized
  2. filtrationThe formed precipitate was filtered off
  3. customdried under vacuum

Sources & evidence

ORD record
ord-1a112e17657947a5b7c3d350d54a3210
Source dataset
uspto-grants-2012_11
Patent number
US08309587B2

Reaction notes

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