Acetic Acid → 2-(2-Thioxo-2,3-dihydro-benzooxazol-5-yl)-propionic acid

HRID 660318Notes

Reaction equation

HRID 660318 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:14][C:13](=[S:15])[NH:12][C:11]=2[CH:16]=1)[CH3:6])C.[OH-].[Na+].C(O)(=O)C>CCO.O>[S:15]=[C:13]1[NH:12][C:11]2[CH:16]=[C:7]([CH:5]([CH3:6])[C:4]([OH:17])=[O:3])[CH:8]=[CH:9][C:10]=2[O:14]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 20319623Ethyl 2-(2-thioxo-2,3-dihydrobenzoxazol-5-yl)propionate

Product 1

HCID 577421532-(2-Thioxo-2,3-dihydro-benzooxazol-5-yl)-propionic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 2-(2-Thioxo-2,3-dihydro-benzooxazol-5-yl)-propionic acid ethyl ester (124 mg) in 90% aq. EtOH was added NaOH (102 mg) at room temperature. After stirred for 20 h at 45, the reaction mixture was cooled to room temperature, diluted with water. The resulting aqueous layer was acidified with acetic acid and then extracted with dichloromethane. The combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. (105 mg, 95.4%)

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2b8bbd5a8b714e7580e6c247a35ba453
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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