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

HRID 1654949Notes

Reaction equation

HRID 1654949 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-e1fad93779894fe392486ef04cbd5d98
Source dataset
uspto-grants-1995_04
Patent number
US05409956

Reaction notes

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