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ChemicalBook CAS DataBase List DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE

DIETHYL 5-AMINO-3-METHYL-2,4-THIOPHENEDICARBOXYLATE synthesis

2synthesis methods
-

Yield: 84%

Reaction Conditions:

Stage #1:ethyl acetoacetate;ethyl 2-cyanoacetate with ammonium acetate in tolueneReflux;Green chemistry;Gewald Aminoheterocycles Synthesis;
Stage #2: with sulfur at 60; for 4 h;Ionic liquid;Green chemistry;Gewald Aminoheterocycles Synthesis;

Steps:

4-Aryl-2-aminothiophenes (5a-g) and 4-Alkoxy-2-aminothiophenes(8a-h)
General procedure: A mixture of 2-(1-ethoxyethylidene)malononitrile[27] (7b, 272 mg, 2 mmol),sulfur (64 mg, 2 mmol), and basic ionic liquid (bmIm)OH (380 mg, 2.4 mmol) was allowed to stir at 60°C for 4 h. The reaction mixture was cooled to room temperature and washed with diethyl ether or ethyl acetate (330 mL), and organic layers were concentrated to 1/4 of the volume and kept in a refrigerator. The precipitate that formed was filtered and dried.

References:

Kaki, Venkata Rao;Akkinepalli, Raghuram Rao;Deb, Pran Kishore;Pichika, Mallikarjuna Rao [Synthetic Communications,2015,vol. 45,# 1,p. 119 - 126]