Reacción #1119121

Ecuación de reacción

triethylamine

1,1,3-trimethylindane-4-amine

2-methyl-3furan carboxylic acid

thionyl chloride

→

white crystals

Rendimiento 65.0%

2-methyl N-(1,1,3-trimethylindan-4-yl)-3-furan carboxamide

Rendimiento 65.0%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas refluxed for 1 hour
2. 2
   workup.DISTILLATIONThe reaction solution was distilled under reduced pressure
3. 3
   Otroto remove excess thionyl chloride
4. 4
   TemperaturaThe obtained residue was cooled
5. 5
   LavadoThe reaction solution was sequentially washed with water and brine
6. 6
   OtroThe organic layer consequently separated
7. 7
   Secadowas dried with magnesium sulfate
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe concentrated residue was purified
10. 10
    Otroby being recrystallized with ethyl acetate/n-hexane

Procedimiento

A mixture of 1.5 g (11.9 mmols) of 2-methyl-3furan carboxylic acid with 3 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The obtained residue was cooled and 20 ml of ethyl acetate, 2 g (19.8 mmols) of triethylamine, and 1.8 g (10.3 mmols) of 1,1,3-trimethylindane-4-amine were added thereto. The resultant mixture was stirred at room temperature for 2 hours. The reaction solution was sequentially washed with water and brine. The organic layer consequently separated was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was purified by being recrystallized with ethyl acetate/n-hexane, to obtain 1.8 g of white crystals (Compound No. 17 shown in Table 6). The yield was 65%.

Fuente