Thiophenol → 1-(Phenylthio)pyrrolidine-2,5-dione

HRID 260476ノート

反応式

HRID 260476 の反応式
Cl[N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]1([SH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[C:9]1([S:15][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:8])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 31398Chlorosuccinimide2 回

生成物 1

HCID 3617741-(Phenylthio)pyrrolidine-2,5-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a partial solution of N-chlorosuccinimide (3.34 g, 25 mmol) in dry methylene chloride (30 mL), cooled in an ice bath and under an inert atmosphere, was added thiophenol (2.05 mL, 20 mmol) via syringe. After stirring for 1 hour, additional N-chlorosuccinimide (0.40 g, 3 mmol) was added. After 2.5 hours total, triethylamine (3.9 mL, 28 mmol) was added dropwise. Within 15 minutes the reaction mixture was diluted with methylene chloride, the solvent washed with dilute aq. HCl and the solvent then dried (Na2SO4), filtered through a pad of charcoal and evaporated. The residue was triturated with diethyl ether and the product collected by filtration to yield the title compound mp 115°-116° C. [lit. mp 115°-116° C., J. Org. Chem., 34, 51 (1969)]. This material was used as is.

後処理

  1. waitAfter 2.5 hours total
  2. washthe solvent washed with dilute aq. HCl
  3. dry with materialthe solvent then dried (Na2SO4)
  4. filtrationfiltered through a pad of charcoal
  5. customevaporated
  6. customThe residue was triturated with diethyl ether
  7. filtrationthe product collected by filtration

出典と根拠

ORDレコード
ord-1cdca9b0108b469eb8fecd095c52da43
出典データセット
uspto-grants-1996_06
特許番号
US05527819

反応ノート

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