4-Toluenesulfonyl chloride → HCID 20814155, compound

HRID 896014Notes

Reaction equation

HRID 896014 reaction equation
[CH3:1][C:2]1[N:12]2[C:13]3[C:8]([O:9][CH2:10][CH:11]2[CH2:14][OH:15])=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1>[CH3:1][C:2]1[N:12]2[C:13]3[C:8]([O:9][CH2:10][CH:11]2[CH2:14][O:15][S:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=2)(=[O:24])=[O:23])=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 22349482HCID 22349482, compound

Product 1

HCID 20814155HCID 20814155, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(2-Methyl-3,4-dihydro-5-oxa-1,2a-diaza-acenaphthylen-3-yl)-methanol (2.0 g, 9.8 mmole) was dissolved in pyridine (35 mL), p-toluenesulfonyl chloride (4.0 g, 20.9 mmole) was added and the resulting mixture was stirred at room temperature overnight. The solvent was removed and the residue partitioned between 400 mL each of methylene chloride and saturated aqueous sodium bicarbonate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuum. The crude residue was column chromatographed on silica gel using methylene chloride to elute 2.6 g of the title compound. 1H NMR (DMSO-d6): δ 7.60 (d, 1H); 7.20 (m, 3H); 7.05 (t, 1H); 6.65 (d, 1H); 4.75 (d, 1H); 4.57 (dd, 1H); 4.10 (m, 3H); 2.58 (s, 3H); 2.47 (s, 3H).

Workup

  1. customThe solvent was removed
  2. customthe residue partitioned between 400 mL each of methylene chloride and saturated aqueous sodium bicarbonate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on silica gel
  8. washto elute 2.6 g of the title compound

Sources & evidence

ORD record
ord-d9ddc44495d943e2bed6d64717f7fa1d
Source dataset
uspto-grants-2005_07
Patent number
US06919334B2

Reaction notes

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