Reacción #75141

Ecuación de reacción

1-bromo-3-chloropropane

1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

sodium hydride

→

1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

Rendimiento 44.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe whole is cooled to 0°-5° C.
2. 2
   workup.STIRRINGUpon completion, stirring
3. 3
   workup.WAITis continued for 3 hours at room temperature
4. 4
   workup.ADDITIONThe reaction mixture is poured
5. 5
   Otroonto crushed ice
6. 6
   Extracciónthe product is extracted with methylbenzene
7. 7
   LavadoThe extract is washed with water
8. 8
   Otrodried
9. 9
   Filtraciónfiltered
10. 10
    Otroevaporated
11. 11
    OtroThe residue is crystallized from 2-propanol

Procedimiento

To a stirred solution of 8.5 parts of 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one in 45 parts of N,N-dimethylformamide are added portionwise 1.7 parts of a sodium hydride dispersion 78%. After stirring for 1 hour at room temperature, the whole is cooled to 0°-5° C. and 8.65 parts of 1-bromo-3-chloropropane are added dropwise (slowly). Upon completion, stirring is continued for 3 hours at room temperature. The reaction mixture is poured onto crushed ice and the product is extracted with methylbenzene. The extract is washed with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 5.5 parts (44%) of 1-(3-chloropropyl)-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one; mp. 115° C.

Fuente