Hydrogen Bromide → HCID 53983958, compound

HRID 1389565Notes

Reaction equation

HRID 1389565 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=1[O:18]C)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.I.Br>C(O)(=O)C>[CH2:1]([C:8]1[CH:13]=[C:12]([C:14]([CH3:16])([CH3:15])[CH3:17])[CH:11]=[CH:10][C:9]=1[OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24841Hydrogen iodideHCID 54162180HCID 54162180, compound

Product 1

HCID 53983958HCID 53983958, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.56 g of the compound obtained in Example 3 (b) above was dissolved in 6 ml of acetic acid and 1.2 ml of 57% hydroiodic acid and 1.0 ml of 47% hydrobromic acid were added thereto, followed by heat-refluxing for 30 hours. The mixture was concentrated under reduced pressure, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried, concentrated, and the residue was chromatographed on silica gel column using a mixed solvent of methylene chloride: ethyl acetate (20:1 by volume) as an eluting agent to obtain 510 mg of the title compound having the following properties.

Workup

  1. temperatureby heat-refluxing for 30 hours
  2. concentrationThe mixture was concentrated under reduced pressure, water
  3. additionwas added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. customdried
  8. concentrationconcentrated
  9. customthe residue was chromatographed on silica gel column

Sources & evidence

ORD record
ord-1c6ff84fb87f4ed4b0f90ec5e46b231d
Source dataset
uspto-grants-1981_01
Patent number
US04245099

Reaction notes

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