Reaction #9814

ord-8f6706cc574948029bb2a0abec2abc5c

Reaction equation

O=S1(=O)CCOc2ccccc21
2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide
O=S(=O)(O)O
H2SO4
O=[N+]([O-])O
nitric acid
→
O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2
title compound
Yield 53.7%
O=[N+]([O-])c1ccc2c(c1)S(=O)(=O)CCO2
6-Nitro-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide
Yield 53.7%

Reactants

O=S1(=O)CCOc2ccccc21
2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide
O=S(=O)(O)O
H2SO4
O=[N+]([O-])O
nitric acid

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe product isolated by filtration

Procedure

2.554 g 66% H2SO4 and 1.454 g 65% nitric acid were mixed at 0° C. 2.395 g 2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide were added in portions at 0° C. After stirring for 30 min. the mixture was diluted with water and the product isolated by filtration. Chromatography on silica yielded 1.6 g of the title compound and 0.37 g 0.58 g of the 8-nitro isomer.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091345B2uspto-grants-2006_08