Phthalic Anhydride → HCID 68469866, compound

HRID 502995Notes

Reaction equation

HRID 502995 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])=[N:5][N:4]=[C:3]1[C:14]([NH2:17])([CH3:16])[CH3:15].[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>C(O)(=O)C>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:6]1[N:2]([CH3:1])[C:3]([C:14]([N:17]2[C:21](=[O:22])[C:20]3[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:18]2=[O:23])([CH3:15])[CH3:16])=[N:4][N:5]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 68466051HCID 68466051, compound

Product 1

HCID 68469866HCID 68469866, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[4-Methyl-5-(2-chlorophenyl)-1,2,4-triazol-3-yl]propan-2-amine (1.19 g) and phthalic anhydride (704 mg) were diluted with acetic acid (5 ml), followed by stirring under heating and refluxing for 22 hours. The reaction solution was subjected to evaporation under reduced pressure and the resulting residue was diluted with ethyl acetate (50 ml) and washed with a saturated aqueous sodium bicarbonate solution (30 ml×2). The organic layer was dried over anhydrous sodium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting solid was recrystallized from ethanol-water to obtain 1.47 g of 2-{1-[5-(2-chlorophenyl)-4-methyl-1,2,4-triazol-3-yl]-1-methylethyl}-1H-isoindole-1,3-(2H)-dione (white solid).

Workup

  1. temperatureunder heating
  2. temperaturerefluxing for 22 hours
  3. customThe reaction solution was subjected to evaporation under reduced pressure
  4. additionthe resulting residue was diluted with ethyl acetate (50 ml)
  5. washwashed with a saturated aqueous sodium bicarbonate solution (30 ml×2)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed by evaporation under reduced pressure
  9. customThe resulting solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-0dc42f58cad24a10b94a59158e6bb32e
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

Loading…