Reacción #169683

Ecuación de reacción

benzene-1,4-diamine

2-chlorobenzo[d]oxazole

→

N-(1,3-benzoxazol-2-yl)benzene-1,4-diamine

Rendimiento 104.0%

Disolventes

NMP

NMP

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Extracciónextracted with ethyl acetate (3×200 mL)
3. 3
   LavadoThe combined organic extracts were washed with brine (150 ml)
4. 4
   Secadodried (Na2SO4)
5. 5
   Filtraciónfiltered
6. 6
   ConcentraciónThe filtrate was concentrated under reduced pressure
7. 7
   OtroThe residue obtained
8. 8
   Otrowas purified by chromatography (silica, methylene chloride to 1:19 methanol/methylene chloride)

Procedimiento

To a solution of benzene-1,4-diamine (5.0 g) in NMP (30 ml) was added dropwise, over 0.5 h, a solution of 2-chlorobenzo[d]oxazole (6.03 g) in NMP (50 ml). After the addition was complete, the mixture was stirred at ambient temperature for 1 h. After this time, the reaction mixture was diluted with water (200 mL) and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine (150 ml), dried (Na2SO4) and filtered. The filtrate was concentrated under reduced pressure. The residue obtained was purified by chromatography (silica, methylene chloride to 1:19 methanol/methylene chloride) to afford N-(1,3-benzoxazol-2-yl)benzene-1,4-diamine (9.20 g) as an off-white solid.

Fuente