Methanesulfonyl chloride → HCID 86658143, compound

HRID 1509848Notes

Reaction equation

HRID 1509848 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH2:11][OH:12])[CH:9]=2)[O:4][CH2:3][CH2:2]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15].C([O-])(O)=O.[Na+]>C(Cl)Cl>[S:1]1[C:10]2[C:5](=[CH:6][N:7]=[C:8]([CH2:11][O:12][S:14]([CH3:13])(=[O:16])=[O:15])[CH:9]=2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 516892Sodium BicarbonateHCID 67424827HCID 67424827, compound

Product 1

HCID 86658143HCID 86658143, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of (2,3-dihydro-4-oxa1-thia-6-aza-naphthalen-7-yl)-methanol (0.150 g, 0.8 mmol; prepared as described in WO 2004/058144) in DCM (4 mL), cooled to 0° C., were added TEA (0.228 mL, 1.6 mmol, 2 eq.) and MsCl (0.076 mL, 0.98 mmol, 1.2 eq.). The reaction was stirred at the same temperature. MsCl (0.013 mL, 0.16 mmol) was added after 30 min. A sat. NaHCO3 solution (25 mL) and DCM (20 mL) were added. The two layers were decanted and the org. layer was dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (DCM-MeOH 97-3) to afford the tittle compound as a yellowish oil (0.210 g, 98% yield).

Workup

  1. customThe two layers were decanted
  2. dry with materiallayer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by CC (DCM-MeOH 97-3)

Sources & evidence

ORD record
ord-84a53bf7b31743ed8dda115c32902e7e
Source dataset
uspto-grants-2012_07
Patent number
US08211890B2

Reaction notes

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