Water → HCID 21190099, compound

HRID 619509Notes

Reaction equation

HRID 619509 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+].Br[CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].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[CH2:17][CH2:18][CH2:19][N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 1358102941,2-Dihydro-3-methyl-1,4,7b-triazacyclopent[cd)inden-2-one

Product 1

HCID 21190099HCID 21190099, compoundYield 31.7%

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 20 minutes at the same temperature. To the reaction mixture was added 13.14 g (50 mmol) of N-(3-bromopropyl)phthalimide. The mixture was stirred for 7 hours at 100° C. After cooling, the reaction mixture was poured into water, which was subjected to extraction with chloroform. The extract was dried over anhydrous magnesium sulfate, and, the solvent was then distilled off. The residue was crystallized from methylene chloride--ethanol to give 5.72 g of the desired compound (31.7%, pale brown solid substance).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe mixture was stirred for 20 minutes at the same temperature
  4. stirringThe mixture was stirred for 7 hours at 100° C
  5. temperatureAfter cooling
  6. extractionwas subjected to extraction with chloroform
  7. dry with materialThe extract was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was then distilled off
  9. customThe residue was crystallized from methylene chloride

Sources & evidence

ORD record
ord-3e32a66a57b7461990ce493b108316aa
Source dataset
uspto-grants-1999_09
Patent number
US05958942

Reaction notes

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