Acetic Acid → 2-(2-Thioxo-2,3-dihydro-benzothiazol-6-yl)-propionic acid

HRID 1626893Notes

Reaction equation

HRID 1626893 reaction equation
C([O:3][C:4](=[O:17])[CH:5]([C:7]1[CH:16]=[CH:15][C:10]2[NH:11][C:12](=[S:14])[S:13][C:9]=2[CH:8]=1)[CH3:6])C.[OH-].[Na+].CC(O)=O>C1COCC1.O>[S:14]=[C:12]1[NH:11][C:10]2[CH:15]=[CH:16][C:7]([CH:5]([CH3:6])[C:4]([OH:17])=[O:3])=[CH:8][C:9]=2[S:13]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 577421502-(2-Thioxo-2,3-dihydro-benzothiazol-6-yl)-propionic acid ethyl ester

Product 1

HCID 577421402-(2-Thioxo-2,3-dihydro-benzothiazol-6-yl)-propionic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(2-Thioxo-2,3-dihydro-benzothiazol-6-yl)-propionic acid ethyl ester (587 mg) in THF (4 mL) and H2O (4 mL) was added NaOH (229 mg) at room temperature. After stirred for 14 h at room temperature, the reaction mixture was acidified with AcOH (pH=4) and diluted with water. The resulting mixture extracted with dichloromethane and the combined organic layer was dried magnesium sulfate, filtered and concentrated in vacuo. (511 mg, 97%, pale yellow solid)

Workup

  1. extractionThe resulting mixture extracted with dichloromethane
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ffbb6d0b73f48c4babe8ab384dd985c
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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