Felbinac → HCID 14126441, compound

HRID 974020Notes

Reaction equation

HRID 974020 reaction equation
[C:1](Cl)(=[O:5])C(Cl)=O.[C:7]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]([CH2:13]C(O)=O)=[CH:9][CH:8]=1.[N-]=[N+]=[N-].[Na+].Cl.[CH3:28][NH:29][OH:30].C([N:33](CC)CC)C>C1C=CC=CC=1.O.C(Cl)Cl>[C:7]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:10]([CH2:13][NH:33][C:1]([N:29]([OH:30])[CH3:28])=[O:5])=[CH:9][CH:8]=1

Participants

9

Reactant 5

HCID 3332FelbinacHCID 8471TriethylamineHCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 77906N-methylhydroxylamine hydrochloride

Product 1

HCID 14126441HCID 14126441, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent2×HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.3 ml, 15 mmol) was added to a suspension of 4-[l,l'biphenyl]ylacetic acid (2.12 g, 10 mmol) in benzene (25 ml), and the mixture was refluxed under nitrogen for 15 minutes. The resulting solution was evaporated and the residue, which solidified, was redissolved in acetone (20 ml). To this solution was added a solution of sodium azide (1.0 g, 15 mmol) in water (10 ml), and the mixture stirred vigorously at room temperature. Benzene (200 ml) was added, and the aqueous layer removed by pipette. The organic solution was then dried (MgsO4), filtered, and after boiling away about 10 ml of the solvent, the mixture was refluxed for one hour. The mixture was concentrated to a yellow Oil, which was dissolved in methylene chloride (50 ml). To this was added a solution prepared by heating N-methylhydroxylamine hydrochloride (0.6 g, 7 mmol) and triethylamine (1.2 ml, 8.6 mmol) in methylene chloride (20 ml). The mixture was stirred for 30 minutes, and the precipitate was collected by filtration and recrystallized from methanol to provide the named compound as 550 mq of white powder, mp 193°-194° C. (dec.).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 15 minutes
  2. customThe resulting solution was evaporated
  3. dissolutionwas redissolved in acetone (20 ml)
  4. customthe aqueous layer removed by pipette
  5. customThe organic solution was then dried (MgsO4)
  6. filtrationfiltered
  7. temperaturethe mixture was refluxed for one hour
  8. concentrationThe mixture was concentrated to a yellow Oil, which
  9. dissolutionwas dissolved in methylene chloride (50 ml)
  10. additionTo this was added a solution
  11. customprepared
  12. stirringThe mixture was stirred for 30 minutes
  13. filtrationthe precipitate was collected by filtration
  14. customrecrystallized from methanol
  15. customto provide the named compound as 550 mq of white powder, mp 193°-194° C. (dec.)

Sources & evidence

ORD record
ord-7157da1df61b47ccb3fca6bc9b6877a9
Source dataset
uspto-grants-1991_11
Patent number
US05066658

Reaction notes

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