Acetone → HCID 45381085, compound

HRID 1402795Notes

Reaction equation

HRID 1402795 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11]1([CH:17]2[CH2:23][C:22](=O)O[C:19](=[O:20])[CH2:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CC(C)=O>C1COCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]2[N:9]3[C:19](=[O:20])[CH2:18][CH:17]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH2:23][C:22]3=[N:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 2978824-Phenyloxane-2,6-dione

Product 1

HCID 45381085HCID 45381085, compoundYield 18.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The solution of commercial 4,5-dichloro-1,2-phenylenediamine (0.38 g) and 3-phenylglutaric anhydride (0.4 g) in THF (1 ml) was heated shortly and kept at rt for 0.5 h. The solvent was removed in vacuo and the residue redissolved in acetic acid (3 ml). The dark solution was heated to reflux overnight. Then all volatiles were removed in vacuo and the residue was heated with ethanol (5 ml). After reccoling to rt the precipitate was collected by filtration, washed with ethanol, and dried to give a crude (0.39 g). The crude was decolorized in boiling acetone solution with activated carbon and filtered over Celite. Concentration of the filtrate and drying of the residue afforded 7,8-dichloro-3-phenyl-3,4-dihydropyrido[1,2-a]benzimidazol-1(2H)-one (0.13 g) as colourless crystals.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in acetic acid (3 ml)
  3. temperatureThe dark solution was heated
  4. temperatureto reflux overnight
  5. customThen all volatiles were removed in vacuo
  6. temperaturethe residue was heated with ethanol (5 ml)
  7. customAfter reccoling to rt
  8. filtrationwas collected by filtration
  9. washwashed with ethanol
  10. customdried
  11. customto give a crude (0.39 g)
  12. filtrationfiltered over Celite
  13. customConcentration of the filtrate and drying of the residue

Sources & evidence

ORD record
ord-cc4aa223431d4da1aefd761ea4ee8359
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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