Water → HCID 21190184, compound

HRID 1068796Notes

Reaction equation

HRID 1068796 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[O:13])[NH:8]3.[H-].[Na+].[C:16]1(=[O:26])[NH:20][C:19](=[O:21])[C:18]2=[CH:22][CH:23]=[CH:24][CH:25]=[C:17]12.O>CN(C=O)C>[CH3:1][C:2]1[N:3]=[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]3[N:5]2[C:6]=1[C:7](=[O:13])[N:8]3[CH2:1][CH2:2][CH2:6][CH2:7][N:20]1[C:16](=[O:26])[C:17]2=[CH:25][CH:24]=[CH:23][CH:22]=[C:18]2[C:19]1=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6809PhthalimideHCID 24758Sodium hydrideHCID 1358102941,2-Dihydro-3-methyl-1,4,7b-triazacyclopent[cd)inden-2-one

Product 1

HCID 21190184HCID 21190184, compoundYield 122.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 8.66 g (50 mmol) of 1,2-dihydro-3-methyl-1,4,7b-triazacyclopent[cd]inden-2-one in 100 ml of DMF was added, while stirring under ice-cooling, 2.20 g (55 mmol) of 60% sodium hydride (dispersion in oil). The mixture was stirred for 15 minutes at the same temperature. To the reaction mixture was added 14.10 g (50 mmol) of phthalimide, which was stirred for 6 hours at 100° C. After cooling, the reaction mixture was then poured into water, extracted with chloroform. The extract solution was dried over anhydrous magnesium sulfate, the solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to give 11.43 g of the desired compound (61.1%, pale yellow solid).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 15 minutes at the same temperature
  4. stirringwas stirred for 6 hours at 100° C
  5. temperatureAfter cooling
  6. extractionextracted with chloroform
  7. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off
  9. customThe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-78fb24034fd94bbcbd582b6ff07f30cb
Source dataset
uspto-grants-2001_06
Patent number
US06251905B1

Reaction notes

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