Reaktion #71070

Reaktionsgleichung

amino-thioxo-acetic acid ethyl ester

1,3-dichloro-propan-2-one

EtOAc

N2

→

title compound

4-Chloromethyl-thiazole-2-carboxylic acid ethyl ester

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux
2. 2
   Waschenthe mixture was washed with sat. aq. NaHCO3 (10 mL)
3. 3
   TrocknenThe organic layer was dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvent removed under reduced pressure
6. 6
   SonstigePurification of the residue by FC (4:1 hept-EA)

Vorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a mixture of amino-thioxo-acetic acid ethyl ester (2.50 g, 18.77 mmol) and 1,3-dichloro-propan-2-one (2.88 g, 21.59 mmol) in toluene (20.0 mL) was stirred for 2 h at reflux. EtOAc (20 mL) was added at rt and the mixture was washed with sat. aq. NaHCO3 (10 mL) followed by brine (20 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a light yellow oil. TLC:rf (4:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.89 min, [M+H]+=206.40.

Quelle