Cesium carbonate → HCID 131724396, compound

HRID 2083907Notes

Reaction equation

HRID 2083907 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[SH:9].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O.C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 10796Cesium carbonate2×HCID 68320Ethyl 3-bromopropionate2×HCID 707302,4-Dichlorobenzenethiol2×

Product 1

HCID 131724396HCID 131724396, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

2,4-Dichlorothiophenol (5.04 g, 28.2 mmol), caesium carbonate (10.1 g, 31 mmol) and ethyl 3-bromopropanoate (4.2 mL, 33 mmol) in acetone (100 mL) were refluxed overnight under N2(g). After filtration and concentration under reduced pressure, the residue was partitioned between dichloromethane and water. After separation, the aqueous phase was extracted once with dichloromethane. Drying and removal of the solvent in vacuo afforded a liquid residue that contained ˜30% (HPLC) of unreacted 2,4-dichlorothiophenol. The mixture was refluxed again with caesium carbonate (4.7 g) and ethyl 3-bromopropanoate (2 mL) in acetonitrile (100 mL) under N2(g) for 2 h. After filtration and concentration under reduced pressure, the residue was dissolved in diethyl ether and washed with 2 M aq. sodium hydroxide and water. Drying and removal of the solvent in vacuo afforded the sub-title compound.

Workup

  1. filtrationAfter filtration and concentration under reduced pressure
  2. customthe residue was partitioned between dichloromethane and water
  3. customAfter separation
  4. extractionthe aqueous phase was extracted once with dichloromethane
  5. customDrying
  6. customremoval of the solvent in vacuo
  7. customafforded a liquid residue that
  8. filtrationAfter filtration and concentration under reduced pressure
  9. dissolutionthe residue was dissolved in diethyl ether
  10. washwashed with 2 M aq. sodium hydroxide and water
  11. customDrying
  12. customremoval of the solvent in vacuo

Sources & evidence

ORD record
ord-a9891dde62e947dcaba49b88ae38428f
Source dataset
uspto-grants-2004_04
Patent number
US06716834B2

Reaction notes

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