Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 22449033, compound

HRID 2186729Notes

Reaction equation

HRID 2186729 reaction equation
[O:1]=[C:2]1[N:7]([CH2:8][CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:6]2[CH:18]=[CH:19][CH:20]=[C:21]([O:22]C3CCCCO3)[C:5]=2[O:4][CH2:3]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[OH:22][C:21]1[C:5]2[O:4][CH2:3][C:2](=[O:1])[N:7]([CH2:8][CH2:9][O:10][CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:6]=2[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22448935HCID 22448935, compound

Product 1

HCID 22449033HCID 22449033, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-oxo-4-(2-(benzyloxy)ethyl)-8-(tetrahydropyrane-2-yloxy)-3,4-dihydro-2H-1,4-benzoxazine (1.89 g) was dissolved in methanol (100 ml), and pyridinium p-toluenesulfonate (126 mg) was added to the resultant solution, and the mixture was refluxed for 12 hours. The solvent was distilled off under reduced pressure, and the residue was poured into a saturated sodium bicarbonate aqueous solution, and then extracted with ethyl acetate. The resultant organic layer was dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography (silica gel:hexane/ethyl acetate=1/1) to obtain the object compound (1.18 g, yield 80%).

Workup

  1. temperaturethe mixture was refluxed for 12 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe residue was poured into a saturated sodium bicarbonate aqueous solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe resultant organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel:hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-4c958ef5fb8e495c9966d2df1620afbf
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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