Thionyl Chloride → HCID 58598870, compound

HRID 546296Notes

Reaction equation

HRID 546296 reaction equation
S(Cl)(Cl)=[O:2].[C:5]1(=[N:16]O)[CH:8]2[CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH:7]2[CH2:6]1>O1CCOCC1>[C:5]1(=[O:2])[CH:8]2[CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[CH:7]2[CH2:6][NH:16]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3729139HCID 3729139, compound

Product 1

HCID 58598870HCID 58598870, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Thionyl chloride (1.9 mL, 26.4 mmol) was added to a solution of 2,2a,7,7a-tetrahydro-cyclobuta[a]inden-1-one oxime (1.5 g, 8.8 mmol) in 1,4-dioxane (44 mL), and stirred overnight at room temperature. The reaction was quenched with saturated aqueous NaHCO3 (100 mL), and extracted with EtOAc (3×50 mL). The organic extracts were washed with brine, dried over MgSO4, and concentrated to give the subtitle compound and its regioisomer, which were used without further purification. MS calculated for C11H11NO+H: 174, observed: 174.

Workup

  1. customThe reaction was quenched with saturated aqueous NaHCO3 (100 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cf48661b97354fa99b74da04b887814d
Source dataset
uspto-grants-2011_05
Patent number
US07935830B2

Reaction notes

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