Methane → HCID 15291360, compound

HRID 1290738Notes

Reaction equation

HRID 1290738 reaction equation
ON=[C:3]1[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2.C.CN(C)C=[O:24]>Cl.CS(C)=O>[CH:16]1[N:14]2[C:15]3[C:3](=[O:24])[C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=4[C:10]=3[NH:11][C:12](=[O:19])[C:13]2=[N:18][CH:17]=1

Participants

6

Reactant 3

HCID 297Methane2×HCID 6228DimethylformamideHCID 178518650HCID 178518650, compound

Product 1

HCID 15291360HCID 15291360, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 679Dimethyl SulfoxideSolvent

Procedure

A suspension of 1.5 g of 10-(hydroxyimino)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 90 ml of approximately 5N aqueous hydrochloric acid solution is stirred while boiling for 7 hours, cooled and then concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 70° C. The product obtained (2 g) is dissolved in 50 ml of dimethylformamide and, after addition of 0.1 g of decolorizing charcoal, the solution is filtered and the filter is then washed 3 times with 30 ml in total of dimethylformamide. The filtrate and the washings are combined, 600 ml of distilled water are added and they are centrifuged. The solid is suspended in 20 ml of distilled water, filtered, washed with 20 ml in total of acetone and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. The product obtained (1.13 g) is dissolved in 115 ml of dimethyl sulphoxide and, after addition of 0.1 g of decolorizing charcoal, the solution is filtered and the filter is then washed twice with 30 ml in total of dimethyl sulphoxide. The filtrate and the washings are combined, 115 ml of distilled water are added and they are centrifuged. The solid is suspended in 20 ml of distilled water, filtered, washed twice with 20 ml in total of acetone and dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 1 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine-4,10-dione is thus obtained, in the form of a red-orange solid melting at 360° C. (decomposition) [N.M.R. spectrum: (200 MHz; DMSO d6 ; d in ppm): 7.42 and 7.55 (2t, J=7 Hz, 2H: --H7 and --H8); 7.52 and 7.72 (2d, J=7 Hz, 1H each: --H6 and --H9); 7.62 and 8.13 (2d, J=1 Hz, 1H each: --H of the imidazole); 13.60 (cplx, 1H: --NH--)].

Workup

  1. temperaturecooled
  2. concentrationconcentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 70° C
  3. customThe product obtained (2 g)
  4. filtrationthe solution is filtered
  5. washthe filter is then washed 3 times with 30 ml in total of dimethylformamide
  6. addition600 ml of distilled water are added
  7. filtrationfiltered
  8. washwashed with 20 ml in total of acetone
  9. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C
  10. customThe product obtained (1.13 g)
  11. filtrationthe solution is filtered
  12. washthe filter is then washed twice with 30 ml in total of dimethyl sulphoxide
  13. addition115 ml of distilled water are added
  14. filtrationfiltered
  15. washwashed twice with 20 ml in total of acetone
  16. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-79473ef171e04a62b33f76ba44ecb262
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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