Ammonia → HCID 25184774, compound

HRID 1878069Notes

Reaction equation

HRID 1878069 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.[Cl:17][CH2:18][C:19](Cl)=O>>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[N:13]=[C:19]([CH2:18][Cl:17])[O:15][N:14]=2)=[CH:10][CH:11]=1)=[O:4]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 6577Chloroacetyl chlorideHCID 137068883HCID 137068883, compound

Product 1

HCID 25184774HCID 25184774, compound

Procedure

Compound of example 4 (0.500 g, 2.18 mmol) was heated in chloroacetyl chloride (2 mL) at a temperature in the range of 100-110° C. for 4 hours. The reaction mixture was cooled, poured over ice water, basified With ammonia solution, and extracted with ethyl acetate (3×60 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 (35%-50%) as eluent, and the pure fractions were concentrated and crystallized using chloroform/ petroleum ether, to obtain the title compound.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (3×60 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. concentrationthe pure fractions were concentrated
  9. customcrystallized

Sources & evidence

ORD record
ord-e4f28d44955348299df5bd33dfefcc4e
Source dataset
uspto-grants-2012_11
Patent number
US08314103B2

Reaction notes

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