m-Chloroperbenzoic acid → HCID 66747198, compound

HRID 471742Notes

Reaction equation

HRID 471742 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[C:17]2[C:16]([NH2:18])=[N:15][S:14](=[O:20])(=[O:19])[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1.C1C=C(Cl)C=C(C(OO)=[O:29])C=1>C(Cl)Cl.CC(O)=O>[CH3:1][S:2]([CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[C:17]2[C:16]([NH2:18])=[N:15][S:14](=[O:19])(=[O:20])[NH:13][C:12]=2[CH:11]=[CH:10][CH:9]=1)=[O:29]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66746702HCID 66746702, compound

Product 1

HCID 66747198HCID 66747198, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

To a solution of 5-(4-(methylthio)butoxy)-1H-benzo[c][1,2,6]thiadiazin-4-amine-2,2-dioxide (Example 244) (79 mg, 0.25 mmol) in DCM/CH3CO2H (20:1, 20 mL) was added MCPBA (1.0 equiv.) at room temperature. The reaction mixture was then stirred at room temperature overnight. The solvent was evaporated under reduced pressure, and the residue was purified by chromatography on silica gel eluting with 15% MeOH in dichloromethane to give the title compound (74 mg, 90%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.74-1.77 (m, 2H), 1.88-1.95 (m, 2H), 2.50 (s, 3H), 2.68-2.73 (m, 1H), 2.77-2.83 (m, 1H), 4.19 (t, 2H), 6.58-6.60 (d, J=8.4 Hz, 1H), 6.73-6.75 (d, J=8.0 Hz, 1H), 7.44 (t, J=8.0 Hz, 1H), 7.79 (s, 1H), 8.33 (s, 1H), 10.92 (s, 1H). MS 332 (MH+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel eluting with 15% MeOH in dichloromethane

Sources & evidence

ORD record
ord-d5b6739d402045239a5d3365522cbc66
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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