Water → HCID 59676099, compound

HRID 2040457Notes

Reaction equation

HRID 2040457 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:15][C:14]3[C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[S:11][CH2:10][CH2:9][C:8]=3[C:7]=2[CH:20]=1.C1OCCOCCOCCOCCOCCOC1.O>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[NH:15][C:14]3[C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[S:11][CH:10]=[CH:9][C:8]=3[C:7]=2[CH:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2855718-Crown-6HCID 59676097HCID 59676097, compound

Product 1

HCID 59676099HCID 59676099, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

9-Methoxy-6,7-dihydro-12H-5-thia-12-aza-dibenzo[a,e]azulene (57 mg, 0.203 mmoL) in DMF (2 mL) was treated with KO2 (58 mg, 0.811 mmoL) and 18-Crown-6 (54 mg, 0.203) and the reaction mixture was stirred at room temperature for 6 hours. Water was added to quench the reaction. The mixture was then partitioned between EtOAc and saturated NH4Cl. The aqueous phase was extracted two times with EtOAc. The organic layer from each extraction was combined, washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was then purified by column chromatography (silica gel, 1:1 hexanes:EtOAc as eluent) to yield the title compound as a brown solid.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe mixture was then partitioned between EtOAc and saturated NH4Cl
  4. extractionThe aqueous phase was extracted two times with EtOAc
  5. extractionThe organic layer from each extraction
  6. washwashed with water, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto yield a brown oil
  11. customThe crude material (the oil) was then purified by column chromatography (silica gel, 1:1 hexanes:EtOAc as eluent)

Sources & evidence

ORD record
ord-78fbd50ecb5d4af498c1095d36ce619f
Source dataset
uspto-grants-2013_11
Patent number
US08580840B2

Reaction notes

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