Dimethylacetamide → HCID 19813498, compound

HRID 467138Notes

Reaction equation

HRID 467138 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([S:9][C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.[CH3:22][C:23](N(C)C)=[O:24]>O1CCCC1>[C:23]([C:12]1[S:11][C:10]([S:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=2)=[CH:14][CH:13]=1)(=[O:24])[CH3:22]

Participants

5

Reactant 3

HCID 31374DimethylacetamideHCID 19813479HCID 19813479, compoundHCID 178418339Butyllithium

Product 1

HCID 19813498HCID 19813498, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 2-(3-trifluoromethylphenylthio)thiophene (4.0 g) in dry tetrahydrofuran (30 ml) at -30° C. under nitrogen, was added dropwise n-butyllithium (9.2 ml, 2.5M) and the solution left to stir at -30° C. for 2 hours. Dimethylacetamide (2.8 ml) was then added dropwise and the reaction mixture stirred at -30° C. for a further hour, allowed to warm to room temperature and stirred over night. The reaction mixture was quenched with 2N HCl (100 ml), extracted with ether (2×100 ml), dried over MgSO4 and evaporated to give a brown oil. The oil was flash chromatographed on a Sorbsil C60-40/60H column using 30% ether-hexane to give a colourless oil which crystallised on standing.

Workup

  1. waitthe solution left
  2. stirringthe reaction mixture stirred at -30° C. for a further hour
  3. temperatureto warm to room temperature
  4. stirringstirred over night
  5. customThe reaction mixture was quenched with 2N HCl (100 ml)
  6. extractionextracted with ether (2×100 ml)
  7. dry with materialdried over MgSO4
  8. customevaporated
  9. customto give a brown oil
  10. customchromatographed on a Sorbsil
  11. customto give a colourless oil which
  12. customcrystallised

Sources & evidence

ORD record
ord-dc097cbb87284b3e9be2ea0672e656d0
Source dataset
uspto-grants-1992_10
Patent number
US05158971

Reaction notes

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