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

HRID 260476노트

반응식

HRID 260476 반응식
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

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 31398Chlorosuccinimide2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cdca9b0108b469eb8fecd095c52da43
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05527819

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