Potassium ethylxanthate → 2-(2-Thioxo-2,3-dihydro-benzothiazol-6-yl)-propionic acid ethyl ester

HRID 1626892Notes

Reaction equation

HRID 1626892 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9](Br)[CH:8]=1)[CH3:6])[CH3:2].C(O[C:19]([S-:21])=[S:20])C.[K+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]2[NH:13][C:19](=[S:20])[S:21][C:9]=2[CH:8]=1)[CH3:6])[CH3:2]

Participants

5

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 577421482-(4-Amino-3-bromo-phenyl)-propionic acid ethyl ester

Product 1

HCID 577421502-(2-Thioxo-2,3-dihydro-benzothiazol-6-yl)-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-(4-Amino-3-bromo-phenyl)-propionic acid ethyl ester (1.58 g) in DMF was added potassium ethylxanthate (1.86 g) at room temperature. After stirred with reflux for 14 h, the reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=6:1 to 4:1) to afford the product as yellow oil. (595 mg, 38.3%)

Workup

  1. temperaturewith reflux for 14 h
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=6:1 to 4:1)

Sources & evidence

ORD record
ord-fc20f19469c349c68e394d2f63d1dbae
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

Loading…