Hexane → HCID 814117, compound

HRID 1772849Notes

Reaction equation

HRID 1772849 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[NH2:19].CCCCCC.CCOC(C)=O>O1CCOCC1.O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH:19][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:12])=[O:11])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 155402-Nitrobenzenesulfonyl chlorideHCID 227703,4-Dimethoxyaniline

Product 1

HCID 814117HCID 814117, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-nitrobenzenesulfonyl chloride (3.0 g, 13.5 mmol) and 3,4-dimethoxyaniline (2.1 g, 14.9 mmol) in 1,4-dioxane (30 mL) in a sealed reaction tube was heated at 80° C. for 24 h with TLC monitoring (hexane: EtOAc, 1:1). The reaction mixture was diluted with H2O (30 mL), extracted with EtOAc (3×100 mL) and the combined organic phases dried over Na2SO4, filtered and concentrated in vacuo. Purification by gradient flash chromatography, eluting with 20-25% EtOAc in hexane yielded the title compound (2.5 g, 7.39 mmol).

Workup

  1. customin a sealed reaction tube
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialthe combined organic phases dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by gradient flash chromatography
  7. washeluting with 20-25% EtOAc in hexane

Sources & evidence

ORD record
ord-8d9e535e024b46e69dc42f6a493a1e6e
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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