* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of the Chemical Society, 1956, p. 2058,2060
[2] Chemische Berichte, 1953, vol. 86, p. 1295,1301
[3] Journal of the Chemical Society, 1956, p. 2058,2060
[4] Chemische Berichte, 1953, vol. 86, p. 1295,1301
With hydrogen;palladium/active carbon; In methanol; at 50℃; for 16h;
Five-percent palladium on carbon (0.50 g) was added to a solution of 4.00 g of ethyl 3-amino-4-nitro-benzoate in 100 ml of methanol, and the mixture was stirred in a hydrogen atmosphere at 50 C. for 16 hours.. The solid material was separated through filtration, and the filtrate was concentrated to obtain ethyl 3,4-diaminobenzoate..
With polyphosphoric acid; In ethylene glycol;Reflux;
General procedure: Compound 3 (10 mmol) was dissolved in ethylene glycol (50 mL) andthen compound 2 (10 mmol) and a small amount of polyphosphoricacid were added to the stirred solution which was then refluxed forseveral hours (the reaction was monitored by TLC). On completion ofthe reaction, the mixture was poured into ice water. The solution wastreated with 30% sodium hydroxide to slight alkalinity (pH = 9). Theprecipitated solid was filtered off, recrystallised from ethanol anddried in vacuo to give compound 4.
Ethyl 2-(5-methyl-1,3-thiazol-2-yl)-1H-1,3-benzodiazole-6-carboxylate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
66%
With trichlorophosphate; for 3h;Inert atmosphere; Reflux;
General procedure: The mixture of ethyl 3,4-diaminobenzoate 19 (1 eq., 7.34 mmol) and appropriate benzoic acid (1 eq., 7.34 mmol) was put under argon atmosphere and 15 mL of POCl3 were added. The whole was heated at reflux for 3 h. The mixture was cooled to room temperature, poured on ice and neutralized with 6 M NaOH (80 mL), then brought to pH ca. 9 by addition of 20 g of solid NaHCO3. 100 mL of CHCl3 were added and phases were separated. Aqueous phase was extracted with CHCl3 (2×50 mL). Combined organic phases were purified by chromatography on silica gel (CHCl3/MeOH, gradient 0-5 %).
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