Hydrochloric Acid → 7-Benzoyl-3-methyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one

HRID 1283623

반응식

HRID 1283623 반응식
[NH2:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(OCl)(C)(C)C.[CH3:22][S:23][CH:24]([CH3:30])[C:25](OCC)=[O:26].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:4]([C:3]1[CH:12]=[CH:13][CH:14]=[C:15]2[C:2]=1[NH:1][C:25](=[O:26])[C:24]2([CH3:30])[S:23][CH3:22])(=[O:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 760802-AminobenzophenoneHCID 521297Tert-Butyl hypochloriteHCID 3016224Ethyl 2-(methylthio)propionate

생성물 1

HCID 129098167-Benzoyl-3-methyl-3-(methylsulfanyl)-1,3-dihydro-2H-indol-2-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A stirred solution of 3.94 g. (0.02 mole) of 2-aminobenzophenone in methylene chloride at -65°C. was treated with 2.16 g. (0.02 mole) of t-butylhypochlorite. After 15 min. 2.96 g. ethyl α-(methylthio)propionate was added dropwise and stirring continued for 1 hr. At the end of this time 2.02 g. of triethylamine (0.02 mole) was added dropwise and the reaction solution was allowed to warm to room temperature. This was followed by treatment with lN hydrochloric acid and stirred for 15 min. The methylene chloride solution was then separated and stripped under vacuum. The yellow oil residue was triturated with isopropyl ether and 3 g. of a yellow solid was filtered off (51%). Recrystallization from absolute ethanol gave a cream color solid, m.p. 135°-137°C.

후처리

  1. waitcontinued for 1 hr
  2. stirringstirred for 15 min
  3. customThe methylene chloride solution was then separated
  4. customThe yellow oil residue was triturated with isopropyl ether and 3 g
  5. filtrationof a yellow solid was filtered off (51%)
  6. customRecrystallization from absolute ethanol
  7. customgave a cream color solid, m.p. 135°-137°C.

출처 및 근거

ORD 기록
ord-1edd81af83c54d178ce4c422c8199661
출처 데이터셋
uspto-grants-1976_08
특허 번호
US03975531

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