Hydrogen Peroxide → HCID 11481213, compound

HRID 1435867Notes

Reaction equation

HRID 1435867 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[S:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1)=[CH2:2].B.C1C[O:18]CC1.[OH-].[Na+].OO>C1COCC1.O>[OH:18][CH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]2[S:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 68440387HCID 68440387, compound

Product 1

HCID 11481213HCID 11481213, compoundYield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 6-vinyl-4H-benzo[1,4]thiazin-3-one (5.73 g, 30.0 mmole) in dry THF (100 mL) at RT was added 2M BH3.THF (7.5 mL, 15.0 mmole). After 24 h, H2O (15 mL) was slowly added to the reaction mixture followed by 3M NaOH (5 mL) and 30% H2O2 (3.3 mL). After the reaction solution was stirred for 3 h at 50° C., the reaction was concentrated under vacuum. The residue was dissolved in EtOAc and washed with H2O (20 mL) and 1M HCl (20 mL). The organic solution was dried (Na2SO4), concentrated under vacuum, and the remaining solid purified on silica (CH2Cl2/CH3OH, 95:5) afforded the title compound (2.60 g, 41%) as light yellow solid: LC-MS (ES): m/e 210 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated under vacuum
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with H2O (20 mL) and 1M HCl (20 mL)
  4. dry with materialThe organic solution was dried (Na2SO4)
  5. concentrationconcentrated under vacuum
  6. customthe remaining solid purified on silica (CH2Cl2/CH3OH, 95:5)

Sources & evidence

ORD record
ord-2bdfdb3eae8b4779b74bb31b91b87bf0
Source dataset
uspto-grants-2009_11
Patent number
US07618959B2

Reaction notes

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