1H-2,1-Benzothiazine 2,2-dioxide → 3192-06-1

HRID 1776178Notes

Reaction equation

HRID 1776178 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH:4]=[CH:3][S:2]1(=[O:12])=[O:11]>[Pd].CO>[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[CH2:4][CH2:3][S:2]1(=[O:11])=[O:12]

Participants

4

Reactant 1

HCID 218161521H-2,1-Benzothiazine 2,2-dioxide

Product 1

HCID 122033353192-06-1Yield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1H-benzo[c][1,2]thiazine 2,2-dioxide (0.381 g, 2.1 mmol) and 10% palladium on carbon (0.05 g) in anhydrous methanol (6 mL) was placed under a hydrogen filled balloon and stirred at room temperature for 17 hours. The mixture was filtered through Celite and concentrated to give a white solid (0.366 g, 95%). 1H NMR (CDCl3, 300 MHz) δ 7.25-7.16 (m, 2H), 7.07-7.01 (m, 1H), 6.76-6.73 (d, 1H, J=8.4 Hz), 3.51-3.46 (t, 2H, J=6.8 Hz), 3.34-3.29 (br t, 1H, J=6.9 Hz).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7227542d6b12413ba89810e6ecefd23f
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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