Ammonia → HCID 25184712, compound

HRID 1878066Notes

Reaction equation

HRID 1878066 reaction equation
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([C:12](=[N:14][OH:15])[NH2:13])=[CH:10][CH:11]=1)=[O:4].N.[C:17](OC(=O)C)(=O)[CH3:18]>O>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[N:13]=[C:17]([CH3:18])[O:15][N:14]=2)=[CH:10][CH:11]=1)=[O:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 137068883HCID 137068883, compound

Product 1

HCID 25184712HCID 25184712, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound of example 4 (5.5 g, 24 mmol) was refluxed in acetic anhydride (10 mL) at a temperature in the range of 115-120° C. for 2 hours. The black colored reaction mixture was cooled, diluted with water, basified with ammonia solution, and extracted with ethyl acetate (3×100 mL). The organic layer was washed with brine, dried over sodium sulfate and concentrated. The crude product obtained was purified over silica gel using ethyl acetate/petroleum ether (25%-50%) as eluent and the semipurified fractions were further purified using methanol/chloroform (0.5% -1%) as eluent. Pure fractions were concentrated and crystallized using chloroform/petroleum ether, to obtain the title compound.

Workup

  1. temperatureThe black colored reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customwas purified over silica gel
  8. customthe semipurified fractions were further purified
  9. concentrationPure fractions were concentrated
  10. customcrystallized

Sources & evidence

ORD record
ord-724c10d5fe54499e984e8ef8c4090265
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

Loading…