Acetic Anhydride → {2-[(Benzenesulfonyl)amino]-1,3-thiazol-4-yl}acetic acid

HRID 127108Notes

Reaction equation

HRID 127108 reaction equation
[OH-].[K+].[C:3]1([S:9]([NH:12][C:13]2[S:14][CH:15]=[C:16]([CH2:18][C:19]([O:21]CC)=[O:20])[N:17]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(OC(=O)C)(=O)C>O>[C:3]1([S:9]([NH:12][C:13]2[S:14][CH:15]=[C:16]([CH2:18][C:19]([OH:21])=[O:20])[N:17]=2)(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14797Potassium HydroxideHCID 717505ethyl {2-[(phenylsulfonyl)amino]-1,3-thiazol-4-yl}acetate

Product 1

HCID 16394950{2-[(Benzenesulfonyl)amino]-1,3-thiazol-4-yl}acetic acidYield 92.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an aqueous solution of potassium hydroxide (5.0 g.) in water (150 ml.) was added ethyl 2-benzenesulfonamidothiazol-4-ylacetate (9.1 g.) at 10° C. with stirring, and the mixture was stirred for 30 minutes at room temperature. The reaction mixture was adjusted to pH 4 to 4.5 with acetic anhydride, and the mixture was stirred under ice-cooling till the crystals precipitated. The crystals were collected by filtration and dried to give 2-benzenesulfonamidothiazol-4-ylacetic acid (7.7 g.), mp 94° to 96° C. (dec.).

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling till the crystals
  4. customprecipitated
  5. filtrationThe crystals were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-6fb2613198e844988502bf2fc789b9e0
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Reaction notes

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