Thionyl Chloride → HCID 13912876, compound

HRID 1789078Notes

Reaction equation

HRID 1789078 reaction equation
[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(Cl)(Cl)=O>C1C=CC=CC=1>[NH2:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([O:9][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13912874HCID 13912874, compound

Product 1

HCID 13912876HCID 13912876, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 5.55 g of 5-amino-2-methoxy-4-nitrobenzoic acid in 40 ml of benzene was added 40 ml of thionyl chloride, and the mixture was refluxed for 4 hours. Subsequently, an excess amount of the thionyl chloride and the solvent were evaporated, the residue was dissolved in 40 ml of benzene, and then 12.3 g of phenol and 15.3 ml of triethylamine were added under ice cooling. The mixture was stirred under ice cooling for 30 minutes and then at room temperature overnight. To the reaction solution were added water and ethyl acetate, the organic layer was washed with 10 aqueous sodium hydroxide solution and water, successively, and then the solvent was evaporated under reduced pressure. The residue was applied on a silica gel column chromatography, and the fractions eluted by benzene were collected and recrystallized from methanol to give the title compound, m.p. 130°-132° C., yield of 2.55 g.

Workup

  1. temperaturethe mixture was refluxed for 4 hours
  2. customSubsequently, an excess amount of the thionyl chloride and the solvent were evaporated
  3. dissolutionthe residue was dissolved in 40 ml of benzene
  4. addition12.3 g of phenol and 15.3 ml of triethylamine were added under ice cooling
  5. customat room temperature
  6. customovernight
  7. additionTo the reaction solution were added water and ethyl acetate
  8. washthe organic layer was washed with 10 aqueous sodium hydroxide solution and water
  9. customsuccessively, and then the solvent was evaporated under reduced pressure
  10. washthe fractions eluted by benzene
  11. customwere collected
  12. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b3e0e8b3d9e24c10a6b7e68172cefca4
Source dataset
uspto-grants-1987_08
Patent number
US04686292

Reaction notes

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