Hydrogen Peroxide → HCID 15702817, compound

HRID 2073205Notes

Reaction equation

HRID 2073205 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:18]3[C:19]4[N:11]([C:12](=S)[NH:13][C:14](=[O:20])[C:15]=4[CH:16]=[N:17]3)[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].OO.[NH2:26][CH2:27][CH2:28][CH2:29][N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>CN(C)C=O.C(Cl)(Cl)Cl.O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:18]3[C:19]4[N:11]([C:12]([NH:26][CH2:27][CH2:28][CH2:29][N:30]5[CH:34]=[CH:33][N:32]=[CH:31]5)=[N:13][C:14](=[O:20])[C:15]=4[CH:16]=[N:17]3)[CH2:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 787361H-Imidazole-1-propanamineHCID 15702769HCID 15702769, compound

Product 1

HCID 15702817HCID 15702817, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 10.0 g of 8-(3-fluorophenyl)-4,5-dihydro-5-thioxo-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3one in 300 ml of N,N-dimethylformamide was added 18.75 ml of 1N sodium hydroxide. The reaction mixture was cooled to 0° C. in an ice bath for 30 minutes, then 6.25 ml of 30% hydrogen peroxide was added to the mixture dropwise. The mixture was stirred at 0° C. for one hour and 30 minutes then 12.5 ml of N(3-aminopropyl)imidazole was added in one portion. The mixture was allowed to warm to room temperature over 32 hours. The mixture was filtered to remove the solid which was washed with water. The filtrate and wash was evaporated in vacuo to give a yellow solid. The solid was dissolved in 250 ml of chloroform then 100 ml of water was added to give a precipitate. The layers were separated and the precipitate was collected by filtration to give a white solid. The solid was recrystallized from dimethylsulfoxide and dried in vacuo at 60° C. to give 1.1 g of the product of the example as a white solid, m.p. 256°-258° C.

Workup

  1. temperatureto warm to room temperature over 32 hours
  2. filtrationThe mixture was filtered
  3. customto remove the solid which
  4. washwas washed with water
  5. washThe filtrate and wash
  6. customwas evaporated in vacuo
  7. customto give a yellow solid
  8. customto give a precipitate
  9. customThe layers were separated
  10. filtrationthe precipitate was collected by filtration
  11. customto give a white solid
  12. customThe solid was recrystallized from dimethylsulfoxide
  13. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-e78979294d9e4cc493f8b655985aa9f8
Source dataset
uspto-grants-1990_04
Patent number
US04916137

Reaction notes

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