Reaction #11527

Reaction equation

1-thiophen-2-yl-ethylamine

methyl thiophen-2,5-dicarboxylate

1-hydroxybenzotriazole hydrate

N′-(3-dimethylaminopropyl)-N-ethylcarbodiimid hydrochloride

→

5-(1-Thiophen-2-yl-ethylcarbamoyl)-thiophene-2-carboxylic acid methyl ester

Yield 84.0%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.STIRRINGis subsequently stirred at ambient temperature overnight
2. 2
   OtherThe product is isolated
3. 3
   Otherafter acidic work-up and purification on silica gel as waxy solid in 84% yield (0.67 g)

Procedure

A solution of 500 mg (2.7 mmol) of methyl thiophen-2,5-dicarboxylate in CH2Cl2 (20 ml) is treated with 617 mg (4 mmol) 1-hydroxybenzotriazole hydrate and 772 mg (4 mmol) N′-(3-dimethylaminopropyl)-N-ethylcarbodiimid hydrochloride and stirring is continued at ambient temperature for 1 hour. 410 mg (3.2 mmol) of 1-thiophen-2-yl-ethylamine are added to the reaction mixture which is subsequently stirred at ambient temperature overnight. The product is isolated after acidic work-up and purification on silica gel as waxy solid in 84% yield (0.67 g).

Source