Ethyl Acetate → 2-(2-Methanesulfonamido-1,3-thiazol-4-yl)acetic acid

HRID 127103

Reaction equation

HRID 127103 reaction equation
[OH-].[K+].[CH3:3][S:4]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([O:16]CC)=[O:15])[N:12]=1)(=[O:6])=[O:5].C(OCC)(=O)C>O>[CH3:3][S:4]([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=1)(=[O:5])=[O:6]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 3145078Ethyl 2-methanesulfonamidothiazol-4-ylacetate

Product 1

HCID 31595752-(2-Methanesulfonamido-1,3-thiazol-4-yl)acetic acidYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of potassium hydroxide (2.9 g.) in water (80 ml.) was added ethyl 2-methanesulfonamidothiazol-4-ylacetate (9.1 g.) under ice-cooling and stirring, and the mixture was stirred for 1 hour at room temperature. After the reaction, to the reaction mixture was added a mixture of water and ethyl acetate, and then the aqueous layer was separated. The remaining ethyl acetate layer was extracted twice with 10% hydroxide aqueous solution. The extracts were combined with the above obtained aqueous layer, and the mixture was acidified with hydrochloric acid under ice-cooling. The precipitated crystals were collected by filtration, washed with water and dried to give 2-methanesulfonamidothiazol-4-ylacetic acid (5.94 g.), mp 158°-160° C. (dec.).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hour at room temperature
  3. customAfter the reaction
  4. additionto the reaction mixture was added
  5. customthe aqueous layer was separated
  6. extractionThe remaining ethyl acetate layer was extracted twice with 10% hydroxide aqueous solution
  7. temperaturecooling
  8. filtrationThe precipitated crystals were collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-b087c7777af54fa09f7e39a51b4c0f64
Source dataset
uspto-grants-1981_03
Patent number
US04254260

Linked notes

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