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

HRID 2051868

反応式

HRID 2051868 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of 3.94 g. (0.02 mole) of 2-amino-benzophenone 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 1 N 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.

後処理

  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.

出典と根拠

ORDレコード
ord-716342948613447b8563f4f3ca6cd9c9
出典データセット
uspto-grants-1980_01
特許番号
US04182774

関連ノート

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