Ethyl 2-chloro-2-(methylsulfanyl)acetate → Ethyl [2-[(4-chlorophenyl)sulfonylaminomethyl]indan-5-yl]-acetate

HRID 1654949Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654949
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[CH:23](SC)[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(Cl)Cl.C(O)(=O)C.[Zn]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH:13]2[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:19]=3)[CH2:14]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

6

Edukt 2

HCID 10877535Ethyl 2-chloro-2-(methylsulfanyl)acetateHCID 189215132-[(4-Chlorophenyl)sulfonylaminomethyl)indan

Produkt 1

HCID 15290059Ethyl [2-[(4-chlorophenyl)sulfonylaminomethyl]indan-5-yl]-acetateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

16.1 g (50.0 mmol) of [2-[(4-chlorophenyl)sulfonylaminomethyl)indan and 9.27 g (55.0 mmol) of ethyl alpha-chloro-alpha-(methylthio)acetate were dissolved in 50 ml of methylene chloride, to which 6.44 ml (55.0 mmol) of stannic chloride was slowly added dropwise. After stirring for 3 hours, the reaction mixture was poured into ice-water, and the organic phase was collected, washed, dried and condensed. The residue was dissolved in 180 ml of acetic acid, added with 40 g of zinc powder and heated at 110° C. for 1 hour. After cooling, the precipitates were filtrated and washed thoroughly with chloroform and the solvent was removed. The residue was dissolved in 300 ml of ethyl acetate, and washed with water, saturated aqueous sodium bicarbonate solution and water in this order, and dried. The solvent was distilled off under reduced pressure, and the residue was recrystallized from a solvent mixture of ethyl acetate and hexane to obtain 16.7 g of colorless needles. Yield: 82%.

Aufarbeitung

  1. additionwas slowly added dropwise
  2. customthe organic phase was collected
  3. washwashed
  4. customdried
  5. customcondensed
  6. temperatureAfter cooling
  7. filtrationthe precipitates were filtrated
  8. washwashed thoroughly with chloroform
  9. customthe solvent was removed
  10. dissolutionThe residue was dissolved in 300 ml of ethyl acetate
  11. washwashed with water, saturated aqueous sodium bicarbonate solution and water in this order
  12. customdried
  13. distillationThe solvent was distilled off under reduced pressure
  14. customthe residue was recrystallized from a solvent mixture of ethyl acetate and hexane

Quellen und Nachweise

ORD-Eintrag
ord-e1fad93779894fe392486ef04cbd5d98
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05409956

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