Réaction #2186194

ord-e40e81ac9324486888f458ba1be74e4a

Équation de réaction

COC(=O)CC(=O)Cl
chlorocarbonyl-acetic methyl ester
Nc1ccccc1S
2-Amino-thiophenol
CCN(CC)CC
triethylamine
COC(=O)Cc1nc2ccccc2s1
desired product
Rendement 82.0%
COC(=O)Cc1nc2ccccc2s1
Benzothiazol-2-yl-acetic acid methyl ester
Rendement 82.0%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autreto yield a suspension
  2. 2
    Autrethe precipitate removed by filtration
  3. 3
    AutreThe filtrate is evaporated
  4. 4
    Autrecolumn chromatographed (silica gel, ethyl acetate/petroleum ether 1:2)

Mode opératoire

3.2 mL (30 mmol) 2-Amino-thiophenol are dissolved in 100 mL diethylether and treated with 4.17 mL (1 eq.) triethylamine to yield a suspension, to which 3.21 mL (1 eq.) chlorocarbonyl-acetic methyl ester in 10 mL diethylether is added dropwise within 20 min. The resulting suspension is stirred and additional 2 h at room temperature, and the precipitate removed by filtration. The filtrate is evaporated and column chromatographed (silica gel, ethyl acetate/petroleum ether 1:2) to yield the desired product as a yellowish liquid (5.1 g, 82%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07569337B2uspto-grants-2009_08