Reacción #11664

Ecuación de reacción

mono-boc-ortho-phenylenediamine

5-diallylaminomethyl-thiophene-2-carboxylic acid

carbonyldiimidazol

→

{2-[(5-Diallylaminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

Rendimiento 84.3%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated
2. 2
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
3. 3
   LavadoThe organic phase was washed twice with sat. NaHCO3, once with water
4. 4
   Secadodried over Na2SO4
5. 5
   OtroThe solvent was evaporated

Procedimiento

To a solution of 2.70 g (11.38 mmol) 5-diallylaminomethyl-thiophene-2-carboxylic acid in 50 ml THF was added 2.03 g (12.51 mmol) carbonyldiimidazol. After 45 min at rt, 2.48 g (11.95 mmol) mono-boc-ortho-phenylenediamine were added to the reaction mixture, and it was stirred for 3 h at rt. The solvent was evaporated and the residue dissolved in ethyl acetate. The organic phase was washed twice with sat. NaHCO3, once with water and dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (ethyl acetate/heptane 2:8) to yield 4.10 g (9.59 mmol) {2-[(5-Diallylaminomethyl-thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; exact MW [M+H] calc'd: 428.20; MW found [M+H]: 428.3.

Fuente