Acetone → HCID 59597487, compound

HRID 454832Notes

Reaction equation

HRID 454832 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1O)=[N:13][C:12]([F:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2].C(Cl)(=O)C([Cl:21])=O.CN(C)C=O.CC(C)=O>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[Cl:21])=[N:13][C:12]([F:17])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 178469562HCID 178469562, compound

Product 1

HCID 59597487HCID 59597487, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 3a in chloroform were added 4 equivalents of oxalyl chloride followed by 0.1 equiv. of dimethylformamide. The solution was refluxed for 3 hours and was quenched with 5 M sodium hydroxide solution at 4° C. The chloroform layer was collected, washed with 100 mL water and brine solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Product was obtained by recrystallization using acetone. 1H-NMR (CDCl3) δ (ppm): 1.47 (3H, t, J=7.14 Hz), 4.53 (2H, q, J=7.14 Hz), 7.45 (1H, dd, J=8.79, 3.02 Hz), 8.54 (1H, dd, J=9.06, 7.41), 9.21 (1H, s). m/z 255.7 (MH+).

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. customwas quenched with 5 M sodium hydroxide solution at 4° C
  3. customThe chloroform layer was collected
  4. washwashed with 100 mL water and brine solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customProduct was obtained by recrystallization

Sources & evidence

ORD record
ord-c5e784f67e2b4831b8411f8fc58b3bbb
Source dataset
uspto-grants-2013_07
Patent number
US08497262B2

Reaction notes

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