DIMETHYL 2-[DI(METHYLTHIO)METHYLIDENE]MALONATE synthesis
- Product Name:DIMETHYL 2-[DI(METHYLTHIO)METHYLIDENE]MALONATE
- CAS Number:19607-08-0
- Molecular formula:C8H12O4S2
- Molecular Weight:236.31
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Yield:19607-08-0 85 %
Reaction Conditions:
Stage #1: malonic acid dimethyl esterwith potassium carbonate in N,N-dimethyl-formamide at 20;
Stage #2: carbon disulfide in N,N-dimethyl-formamide at 0;
Stage #3: methyl iodide in N,N-dimethyl-formamide at 0 - 20;
Steps:
Preparation of dimethyl 2-(bis(methylthio)methylene)malonate (3)
To a stirred solution of dimethyl malonate (20 mL, 174 mmol) in DMF (120 mL) was added potassium carbonate (48 g, 348 mmol) at room temperature. After the mixture was stirred for 30 min, carbon disulfide (15.78 mL, 261 mmol) was added at 0 °C. After the reaction mixture was stirred for 1 h at 0 °C, methyl iodide (23.8 mL, 383 mmol) was added at 0 °C. The resulting suspension was stirred at room temperature overnight. The mixture was poured into ice water (200 mL) and neutralized by 2 N aqueous HCl. The precipitated solid was collected, washed with water (200 mL) and hexane (200 mL), and dried under high-vacuum to obtain 3 (35 g, 85%) as a white solid; 1H NMR (400 MHz, CDCl3) δ 3.80 (s, 6H), 2.45 (s, 6H).
References:
Shin, Young Sup;Lee, Jun Young;Jeon, Sangeun;Myung, Subeen;Gong, Hyun June;Kim, Seungtaek;Kim, Hyoung Rae;Jeong, Lak Shin;Park, Chul Min [Bioorganic and Medicinal Chemistry Letters,2023,vol. 85,art. no. 129214] Location in patent:supporting information
75-15-0
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108-59-8
630 suppliers
$5.00/25g
19607-08-0
26 suppliers
inquiry