반응 #529720

반응 방정식

triethylamine

2-amino-4'-chlorobenzophenone

t-butyl hypochlorite

ethyl α-(methylthio)-acetate

→

product

수율 33.0%

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

수율 33.0%

용매

methylene chloride

반응 조건

후처리

1. 1
   workup.ADDITIONtreated dropwise with 12.4 g
2. 2
   기타2 hr
3. 3
   기타to come to room temperature
4. 4
   세척The solution was then washed with water
5. 5
   온도to reflux at which time 1N hydrochloric acid
6. 6
   workup.ADDITIONwas added
7. 7
   온도the resulting mixture refluxed overnight
8. 8
   온도The mixture was cooled
9. 9
   기타resulting precipitate
10. 10
    여과filtered off
11. 11
    기타recrystallized from toluene
12. 12
    기타giving 10 g

실험 절차

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.

출처