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

HRID 442538노트

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HRID 442538 반응식
[NH2:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)=[O:5].ClOC(C)(C)C.[CH3:23][S:24][CH2:25][C:26](OCC)=[O:27].C(N(CC)CC)C>C(Cl)Cl>[Cl:12][C:9]1[CH:10]=[CH:11][C:6]([C:4]([C:3]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:2]=2[NH:1][C:26](=[O:27])[CH:25]3[S:24][CH3:23])=[O:5])=[CH:7][CH:8]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 761662-Amino-4'-chlorobenzophenoneHCID 78199Ethyl (methylthio)acetateHCID 521297Tert-Butyl hypochlorite

생성물 1

HCID 129235497-(4-Chlorobenzoyl)-3-methylthioindolin-2-one수율 33%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-65 °C

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.

후처리

  1. additiontreated dropwise with 12.4 g
  2. custom2 hr
  3. customto come to room temperature
  4. washThe solution was then washed with water
  5. temperatureto reflux at which time 1N hydrochloric acid
  6. additionwas added
  7. temperaturethe resulting mixture refluxed overnight
  8. temperatureThe mixture was cooled
  9. customresulting precipitate
  10. filtrationfiltered off
  11. customrecrystallized from toluene
  12. customgiving 10 g

출처 및 근거

ORD 기록
ord-95c3c01a7b854d53aeefb5a48d34f5be
출처 데이터셋
uspto-grants-1977_08
특허 번호
US04045576

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