1-Chloro-4-nitrobenzene → HCID 11543825, compound

HRID 2245806Notes

Reaction equation

HRID 2245806 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([SH:10])[CH:5]=1.Cl[C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.C[O-].[Na+].C(OCC)(=O)C>O1CCCC1.CO>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 74741-Chloro-4-nitrobenzeneHCID 8857Ethyl AcetateHCID 4362804Methyl 3-mercaptobenzoateHCID 10942334Sodium Methoxide

Product 1

HCID 11543825HCID 11543825, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-mercaptobenzoic acid methyl ester (504 mg, 3 mmol) and 1-chloro-4-nitrobenzene (473 mg, 3 mmol) in tetrahydrofuran (4 mL) was added at 0° C., in a dropwise manner, a solution of sodium methoxide in methanol (3.3 mL, 1M). The mixture was heated at reflux for 2 hours with stirring, then cooled to room temperature. Ethyl acetate (25 mL) was added and the mixture was washed consecutively with saturated aqueous sodium hydrogen carbonate (10 mL), distilled water (2×10 mL), and brine (10 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a solid that was recrystallised from ethanol to give the title compound (518 mg, 60%) as a solid, mp 98-100° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. washthe mixture was washed consecutively with saturated aqueous sodium hydrogen carbonate (10 mL)
  4. distillationdistilled water (2×10 mL), and brine (10 mL)
  5. dry with materialThe organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give a solid
  9. customthat was recrystallised from ethanol

Sources & evidence

ORD record
ord-2e7eacc4fd1c4dd187d5a658931e9076
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

Loading…