Toluene → HCID 44180853, compound

HRID 1042033

Reaction equation

HRID 1042033 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[C:14]([C:15](=O)[CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=3[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3][CH2:2]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[C:14]([C:15](=[S:33])[CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=3[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 39732-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-oneHCID 87949Lawesson's reagent

Product 1

HCID 44180853HCID 44180853, compoundYield 135.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A 2 mL conical microwave vial was charged with a magnetic stirring bar, 2-morpholino-8-phenyl-4H-chromen-4-one (LY294002) (150 mg, 488 μmol), Lawesson's reagent (118 mg, 293 μmol), and toluene (2 mL). The reaction mixture was sealed, and the reaction mixture was magnetically stirred and heated via microwave irradiation to 130° C. for 20 minutes. The final mixture was poured onto water (approximately 30 mL), extracted with dichloromethane (3×5 mL), the combined extracts dried over anhydrous magnesium sulfate, filtered and concentrated to dryness. Purification via column chromatography (silica gel; hexanes/ethyl acetate (1:1), then 100% ethyl acetate) afforded pure 2-morpholino-8-phenyl-4H-chromene-4-thione (68) (128 mg, 81% yield).

Workup

  1. additionA 2 mL conical microwave vial was charged with a magnetic stirring bar
  2. customThe reaction mixture was sealed
  3. extractionextracted with dichloromethane (3×5 mL)
  4. dry with materialthe combined extracts dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification via column chromatography (silica gel

Sources & evidence

ORD record
ord-ab050b876fc049279c98c58122f878ad
Source dataset
uspto-grants-2013_10
Patent number
US08557807B2

Linked notes

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