Reacción #529720

Ecuación de reacción

triethylamine

2-amino-4'-chlorobenzophenone

t-butyl hypochlorite

ethyl α-(methylthio)-acetate

→

product

Rendimiento 33.0%

7-(4-Chlorobenzoyl)-3-methylthioindolin-2-one

Rendimiento 33.0%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONtreated dropwise with 12.4 g
2. 2
   Otro2 hr
3. 3
   Otroto come to room temperature
4. 4
   LavadoThe solution was then washed with water
5. 5
   Temperaturato reflux at which time 1N hydrochloric acid
6. 6
   workup.ADDITIONwas added
7. 7
   Temperaturathe resulting mixture refluxed overnight
8. 8
   TemperaturaThe mixture was cooled
9. 9
   Otroresulting precipitate
10. 10
    Filtraciónfiltered off
11. 11
    Otrorecrystallized from toluene
12. 12
    Otrogiving 10 g

Procedimiento

A solution of 23.1 g. (0.1 mole) of 2-amino-4'-chlorobenzophenone in 400 ml. of methylene chloride was cooled to -65° C. and treated dropwise with 12.4 g. (0.1 mole) of t-butyl hypochlorite. After 15 min., 13.4 g. of ethyl α-(methylthio)-acetate (0.1 mole) was added dropwise maintaining -65° C. temperature. After 11/2 hr. 10.1 g. of triethylamine (0.1 mole) was added and the reaction mixture allowed to come to room temperature. The solution was then washed with water and stripped. The residue was taken into methanol and brought to reflux at which time 1N hydrochloric acid was added and the resulting mixture refluxed overnight. The mixture was cooled, resulting precipitate filtered off and recrystallized from toluene, giving 10 g. of a cream colored solid. The product (33% yield) melted at 186°-188° C.

Fuente