ethyl 2-(2-aminothiazol-5-ylthio)acetate synthesis
- Product Name:ethyl 2-(2-aminothiazol-5-ylthio)acetate
- CAS Number:859522-19-3
- Molecular formula:C7H10N2O2S2
- Molecular Weight:218.3
61296-22-8
623-51-8
859522-19-3
General procedure for the synthesis of ethyl 2-(2-aminothiazole-5-thio)acetate from 2-amino-5-bromothiazole hydrobromide and ethyl thioglycolate: In a dry reaction flask, 2-amino-5-bromothiazole hydrobromide (7.26 g, 27.9 mmol), ethyl thioglycolate (10 g, 83.8 mmol) and potassium carbonate (7.7 g, 55.9 mmol) were dissolved in N,N-dimethylformamide (DMF, 25 mL). The reaction mixture was stirred at 50 °C for 2 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble material. Water (150 mL) and ethyl acetate (400 mL) were added to the filtrate, and the organic phase was separated by thorough stirring. The organic phase was washed with saturated brine (3 x 50 mL) and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to give ethyl 2-(2-aminothiazol-5-ylthio)acetate. Yield: 3.3 g (54%). 1H-NMR (DMSO-d6) δ: 7.6 (s, 2H, NH2), 7.00 (s, 1H, thiazole-H), 4.08 (q, 2H, OCH2CH3), 3.45 (s, 2H, SCH2), 1.17 (t, 3H, OCH2CH3).
61296-22-8
264 suppliers
$6.00/1g
623-51-8
241 suppliers
$7.00/25g
859522-19-3
50 suppliers
$282.00/1g
Yield:859522-19-3 68%
Reaction Conditions:
with potassium carbonate in N,N-dimethyl-formamide at 20;
References:
Xu, Jiayi;Lin, Songnian;Myers, Robert W.;Trujillo, Maria E.;Pachanski, Michele J.;Malkani, Sunita;Chen, Hsuan-shen;Chen, Zhesheng;Campbell, Brian;Eiermann, George J.;Elowe, Nadine;Farrer, Brian T.;Feng, Wen;Fu, Qinghong;Kats-Kagan, Roman;Kavana, Michael;McMasters, Daniel R.;Mitra, Kaushik;Tong, Xinchun;Xu, Libo;Zhang, Fengqi;Zhang, Rui;Addona, George H.;Berger, Joel P.;Zhang, Bei;Parmee, Emma R. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 9,p. 2063 - 2068]
3034-22-8
200 suppliers
$7.00/250mg
623-51-8
241 suppliers
$7.00/25g
859522-19-3
50 suppliers
$282.00/1g