Nitric Acid → 6-Nitro-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxide

HRID 9718Notes

Reaction equation

HRID 9718 reaction equation
OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].[O:10]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[S:13](=[O:21])(=[O:20])[CH2:12][CH2:11]1>O>[N+:6]([C:18]1[CH:17]=[CH:16][C:15]2[O:10][CH2:11][CH2:12][S:13](=[O:20])(=[O:21])[C:14]=2[CH:19]=1)([O-:9])=[O:7]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 2107545534257-54-0

Product 1

HCID 219881646-Nitro-2,3-dihydro-benzo[1,4]oxathiine-4,4-dioxideYield 53.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. customthe product isolated by filtration

Sources & evidence

ORD record
ord-8f6706cc574948029bb2a0abec2abc5c
Source dataset
uspto-grants-2006_08
Patent number
US07091345B2

Reaction notes

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