Methyl 4-[(2-ethoxy-2-oxoethyl)-thio]-3-nitrobenzoate synthesis
- Product Name:Methyl 4-[(2-ethoxy-2-oxoethyl)-thio]-3-nitrobenzoate
- CAS Number:188614-00-8
- Molecular formula:C12H13NO6S
- Molecular Weight:299.3
Yield:188614-00-8 93%
Reaction Conditions:
with triethylamine in acetonitrile at 0 - 5; for 0.5 h;
Steps:
Methyl 4-((2-ethoxy-2-oxoethyl)thio)-3-nitrobenzoate
Methyl 4-fluoro-3-nitrobenzoate (10.0 g, 50.2 mmol) was taken up in MeCN (2.0 L) andTEA (7.61 g, 75.38 mmol) was added to it. The reaction mixture was cooled to 0-5 °C andethyl thioglycolate (7.25 g, 62.7 mmol) was added dropwise. The reaction mixture was stirredfor 30 min. at ice cold temperature. Progress of the reaction was monitored by TLC and aftercompletion; the reaction mixture was diluted with EtOAc and washed with saturated solutionof NH4Cl and brine. The organic layer was dried over anhydrous Na2SO4 and evaporatedunder reduced pressure to dryness to give the title compound (14.0 g, 93% yield) as a yellowsolid which was pure enough to be used in the next step without any further purification.
References:
Pryde, David C.;Middya, Sandip;Banerjee, Monali;Shrivastava, Ritesh;Basu, Sourav;Ghosh, Rajib;Yadav, Dharmendra B.;Surya, Arjun [European Journal of Medicinal Chemistry,2021,vol. 209] Location in patent:supporting information
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