p-Toluenesulfonic acid → 2-(4-Morpholinyl)-4H-1-benzopyran-4-one

HRID 1941231Notes

Reaction equation

HRID 1941231 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.S[C:13]1[O:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17](=[O:19])[CH:18]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.CCOC(C)=O>C1C=CC=CC=1.O>[N:24]1([C:13]2[O:14][C:15]3[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=3[C:17](=[O:19])[CH:18]=2)[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8083MorpholineHCID 8857Ethyl AcetateHCID 12475277HCID 12475277, compound

Product 1

HCID 1312552-(4-Morpholinyl)-4H-1-benzopyran-4-oneYield 44.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Part B: Tosic acid (0.4 g, 2 mmol) is added to a solution of 2-mercapto-4H-1-benzopyran-4-one (3.56 g, 20 mmol) and morpholine (2.44 g, 2.44ml, 28 mmol) in benzene (400ml). After refluxing for 4 hours, the reaction mixture is transferred to a separatory funnel containing EtOAc and water. Extracting with EtOAc (2×), washing with combined organic layers with water and brine, and filtering through sodium sulfate yields 4.56 of crude material after evaporation of the solvent. Flash chromatography over silica gel (300 g, 2.5% MeOH/CHCl3, 50 ml fractions) yields 2.07 g of 2-(4-Morpholinyl)-4H-1-benzopyran-4-one (44.8%, fractions 22-32). Mp 160°-1° C.

Workup

  1. temperatureAfter refluxing for 4 hours
  2. customthe reaction mixture is transferred to a separatory funnel
  3. extractionExtracting with EtOAc (2×)
  4. washwashing with combined organic layers with water and brine
  5. filtrationfiltering through sodium sulfate
  6. customyields 4.56 of crude material
  7. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-de7ee2cfbf1443bd8e03b62ec1751220
Source dataset
uspto-grants-1997_12
Patent number
US05703075

Reaction notes

Loading…