Hydrogen Bromide → HCID 178515897, compound

HRID 1722016Notes

Reaction equation

HRID 1722016 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 X), acidified with concentrated HC1, 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). Analysis calculated for C9H6N2BrC10.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperaturethe solution was cooled
  4. extractionextracted with CH2Cl2 (2 X)
  5. concentrationwith concentrated HC1
  6. temperaturecooled
  7. filtrationfiltered
  8. customto yield 100% of crude acid
  9. temperatureat reflux
  10. stirringwith stirring
  11. waitAfter 15 hours
  12. concentrationthe solution was concentrated to dryness
  13. additionthe residue treated with NaHCO3
  14. concentrationThe mixture was concentrated to dryness
  15. customchromatographed on silica gel
  16. washthe product eluted with 5% CH3OH-CHCl3

Sources & evidence

ORD record
ord-2d30360d0ba24aa9a694f3437fb1dc6d
Source dataset
uspto-grants-1989_08
Patent number
US04853383

Reaction notes

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