Hexane → HCID 28552743, compound

HRID 1772850Notes

Reaction equation

HRID 1772850 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)(=[O:14])=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[Sn]Cl.CCCCCC.CCOC(C)=O>C(O)C>[NH2:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:12]([NH:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 24479Stannous ChlorideHCID 814117HCID 814117, compound

Product 1

HCID 28552743HCID 28552743, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-(3,4-dimethoxyphenyl)-2-nitrobenzenesulfonamide (2.5 g, 7.39 mmol) and SnCl2 (8.34 g, 36.9 mmol) in ethanol was heated at 100° C. for 5 h in a sealed tube with TLC monitoring (hexane:EtOAc, 1:1). After concentration in vacuo H2O (30 mL) was added and the mixture was extracted with EtOAc (3×100 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by gradient flash chromatography, eluting with 20-25% EtOAc in hexane yielded the title compound (2.0 g, 6.49 mmol).

Workup

  1. concentrationAfter concentration in vacuo H2O (30 mL)
  2. additionwas added
  3. extractionthe mixture was extracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by gradient flash chromatography
  8. washeluting with 20-25% EtOAc in hexane

Sources & evidence

ORD record
ord-0b87fe014e0741e0a86de1e6d7428165
Source dataset
uspto-grants-2016_02
Patent number
US09249160B2

Reaction notes

Loading…