Hexane → HCID 90030819, compound

HRID 1772860Notes

Reaction equation

HRID 1772860 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]1[N:8]=[C:7]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)(=[O:12])=[O:11])[CH:6]=[CH:5][CH:4]=1.CCCCCC.CCOC(C)=O.C([O-])(O)=O.[Na+]>C(O)(=O)C.[Fe]>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([NH:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N:2]([CH3:22])[CH3:1])[N:8]=1)(=[O:11])=[O:12]

Participants

7

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 118047059HCID 118047059, compound

Product 1

HCID 90030819HCID 90030819, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

In a sealed tube, a mixture of N-[6-(dimethylamino)pyridin-2-yl]-2-nitrobenzenesulfonamide (1.0 g, 3.10 mmol) and Fe powder (0.85 g, 11.5 mmol) in acetic acid (10 mL) was heated at 60° C. for approximately 15 min with TLC monitoring (hexane:EtOAc, 1:1). The reaction mixture was poured into saturated aqueous NaHCO3 solution (100 mL) and extracted with EtOAc (3×50 mL), the combined organic layers were dried over Na2SO4 and concentrated in vacuo. Purification by gradient flash chromatography, eluting with 0-45% EtOAc in hexane yielded the title compound (0.7 g, 2.39 mmol).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customPurification by gradient flash chromatography
  5. washeluting with 0-45% EtOAc in hexane

Sources & evidence

ORD record
ord-19378e8ad5ad49c091cb8a7f541bd05a
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

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