Ethyl Acetate → HCID 19843394, compound

HRID 2352552Notes

Reaction equation

HRID 2352552 reaction equation
C([Li])CCC.[CH2:6]([NH:9][C:10]([C:12]1[S:16][CH:15]=[N:14][CH:13]=1)=[O:11])[CH2:7][CH3:8].[Cl:17][C:18]1[CH:36]=[CH:35][C:21]([O:22][CH2:23][CH2:24]S(C2C=CC(Cl)=CC=2)(=O)=O)=[CH:20][CH:19]=1.C(OC(=O)C)C>CCCCCC.O1CCCC1>[CH2:6]([N:9]([CH2:24][CH2:23][O:22][C:21]1[CH:35]=[CH:36][C:18]([Cl:17])=[CH:19][CH:20]=1)[C:10]([C:12]1[S:16][CH:15]=[N:14][CH:13]=1)=[O:11])[CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 17992063HCID 17992063, compoundHCID 19843393HCID 19843393, compoundHCID 178418339Butyllithium

Product 1

HCID 19843394HCID 19843394, compoundYield 74.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Butyl lithium (1.6 M, 7.5 ml) in hexane was added to a solution of the N-propyl thiazole-5-carboxamide (1.7 g, 10 mmol) obtained in A in tetrahydrofuran (80 ml) at -78° C. under an atmosphere of nitrogen. The resultant solution was stirred for 10 minutes and then allowed to warm to room temperature whereupon the 2-(4-chlorophenoxy)-1-(4-chlorophenylsulphonyl)ethane (5.20 g, 15 mmol) obtained in B dissolved in tetrahydrofuran (40 ml) was added. The resultant solution was then refluxed for 5 days. On cooling, the solvent was evaporated and the residue dissolved in 1:4 water: ethyl acetate (500 ml). The organic layer was washed with saturated sodium chloride solution, dried (MgSO4) and the solvent evaporated to leave an oil which, after flash chromatography on silica gel with 1:2 ethylacetate: petroleum ether as the eluant, yielded the desired product (2.42 g). Mass spectroscopy revealed the mass/charge ratio of the parent molecule ion, M+, to be 324 thereby confirming the molecular weight of the product to be 324.

Workup

  1. customobtained in B
  2. additionwas added
  3. temperatureOn cooling
  4. customthe solvent was evaporated
  5. dissolutionthe residue dissolved in 1:4 water
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated
  9. customto leave an oil which

Sources & evidence

ORD record
ord-5e74127410324ceba323997ff5d19bdb
Source dataset
uspto-grants-1989_10
Patent number
US04877802

Reaction notes

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