Dinitrofluorobenzene → HCID 86591042, compound

HRID 1592011Notes

Reaction equation

HRID 1592011 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][NH:8][S:7]1(=[O:13])=[O:12].C([O-])([O-])=O.[Cs+].[Cs+].F[C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][C:28]=1[N+:36]([O-:38])=[O:37]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[C:10](=[O:11])[CH2:9][N:8]([C:31]2[CH:32]=[CH:27][C:28]([N+:36]([O-:38])=[O:37])=[CH:29][C:30]=2[N+:33]([O-:35])=[O:34])[S:7]1(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 10796Cesium carbonateHCID 66751042HCID 66751042, compound

Product 1

HCID 86591042HCID 86591042, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the title B compound, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (303 mg, 1.05 mmol) in dry 1,4-dioxane (5 mL) is treated with Cs2CO3 (342 mg, 1.05 mmol). 1-Fluoro-2,4-dinitrobenzene (197 mg, 1.05 mmol) is added and the mixture is stirred at RT for 16 h. The solvent is evaporated and the residue is partitioned between EtOAc and 1N aqueous HCl. The organic layer is dried over anhydrous Na2SO4 and concentrated. The residue is chromatographed on silica gel using 10%→100% EtOAc in hexanes as the eluent to afford 2-(2,4-dimethoxybenzyl)-5-(2,4-dinitrophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one as a yellow solid: [M−1]−=451.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is partitioned between EtOAc and 1N aqueous HCl
  3. dry with materialThe organic layer is dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel using 10%→100% EtOAc in hexanes as the eluent

Sources & evidence

ORD record
ord-e4b18b4a7aea4c73b66df6e0058491f1
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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