Hydrogen Bromide → HCID 178515897, compound

HRID 235966Notes

Reaction equation

HRID 235966 reaction equation
[Br:1][C:2]1[NH:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[C:9]([Cl:15])[CH:8]=2)=[N:4][C:3]=1C(F)(F)F.[OH-].[Na+].Br>CC(O)=O>[Br:1][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([Cl:15])[CH:8]=2)[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 178488960HCID 178488960, compound

Product 1

HCID 178515897HCID 178515897, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 56 (7.4 g, 0.021 mol) and 10% NaOH (200 ml) was heated at reflux with stirring. After 4 hours, the solution was cooled, extracted with CH2Cl2 (2×), acidified with concentrated HCl, cooled and filtered to yield 100% of crude acid. The crude acid (6.9 g, 0.021 mol), AcOH (40 ml) and 48% HBr (160 ml) were heated at reflux with stirring. After 15 hours, the solution was concentrated to dryness and the residue treated with NaHCO3. The mixture was concentrated to dryness and the residue combined with silica gel and chromatographed on silica gel and the product eluted with 5% CH3OH--CHCl3 to yield 3.0 g (53%) of 57, m.p. 225°-27° C. (CH3CN).

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe solution was cooled
  4. extractionextracted with CH2Cl2 (2×)
  5. temperaturecooled
  6. filtrationfiltered
  7. customto yield 100% of crude acid
  8. temperatureat reflux
  9. stirringwith stirring
  10. waitAfter 15 hours
  11. concentrationthe solution was concentrated to dryness
  12. additionthe residue treated with NaHCO3
  13. concentrationThe mixture was concentrated to dryness
  14. customchromatographed on silica gel
  15. washthe product eluted with 5% CH3OH

Sources & evidence

ORD record
ord-c5ebda72836e4bf8b1cc18eb51c3400b
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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