Dimethyl Sulfoxide → HCID 18975447, compound

HRID 2393413Notes

Reaction equation

HRID 2393413 reaction equation
[CH:1]1[N:5]2[C:6]3[CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:7]=3[NH:8][C:9](=[O:10])[C:4]2=[N:3][CH:2]=1.CS(C)=O.O.[C:23]([OH:27])(=[O:26])[CH:24]=[O:25].[H-].[Na+]>O.C(O)(=O)C>[O:10]=[C:9]1[NH:8][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[CH:17]([CH:24]([OH:25])[C:23]([OH:27])=[O:26])[C:6]=2[N:5]2[CH:1]=[CH:2][N:3]=[C:4]12

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 18975447HCID 18975447, compoundYield 63.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred mixture of 6.7 g of 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one, 140 ml of dimethyl sulphoxide and 4.15 g of glyoxylic acid monohydrate, under an argon atmosphere, are added portionwise 4.95 g of 80% sodium hydride while maintaining the temperature at about 20° C. The stirring is continued for 18 hours, and the reaction medium is acidified using acetic acid (11 ml) and is heated at a temperature in the region of 80° C. for 2 hours. The reaction mixture is filtered and the solid is washed with acetone (3×75 ml), with methanol (75 ml), again with acetone (2×75 ml) and dried under vacuum (1 mmHg; 0.13 kPa). The light-beige-coloured solid obtained (10.1 g) is dissolved in 500 ml of distilled water and the aqueous solution is washed with ethyl acetate (2×100 ml), then treated with 0.5 g of animal black and filtered. The filtrate is acidified with 45 ml of 1N hydrochloric acid and the precipitate formed is filtered off, washed with distilled water (50 ml) and with acetone (3×75 ml), and dried at 70° C. under vacuum (1 mmHg; 0.13 kPa). 5.7 g of (4,5-dihydro-4-oxo-10H-imidazo(1,2-a]indeno[1,2-e]pyrazin-10-yl)glycolic acid are obtained in the form of a pale yellow solid melting above 260° C. (1H NMR spectrum (200 MHz, (CD3)2 SO-d6, δ in ppm): 4.60 (d, J=3 Hz, 1H: H 10); 5.09 (d, J=3 Hz, 1H: CHO); 5.60 (broad mult., 1H: OH); from 7.25 to 7.50 (mt, 2H: H 7 and H 8); 7.45 and 7.85 (2 broad d, J=7.5 Hz, 1H each: H 6 and H 8); 7.57 and 8.23 (2 broad s, 1H each: H of the imidazole); 12.35 (broad s, 1H: NH 5)).

Workup

  1. temperatureis heated at a temperature in the region of 80° C. for 2 hours
  2. filtrationThe reaction mixture is filtered
  3. washthe solid is washed with acetone (3×75 ml), with methanol (75 ml), again with acetone (2×75 ml)
  4. customdried under vacuum (1 mmHg; 0.13 kPa)
  5. customThe light-beige-coloured solid obtained (10.1 g)
  6. washthe aqueous solution is washed with ethyl acetate (2×100 ml)
  7. additiontreated with 0.5 g of animal black
  8. filtrationfiltered
  9. customthe precipitate formed
  10. filtrationis filtered off
  11. washwashed with distilled water (50 ml) and with acetone (3×75 ml)
  12. customdried at 70° C. under vacuum (1 mmHg; 0.13 kPa)

Sources & evidence

ORD record
ord-4e4429ec807249eeb7447bf9cff5ff43
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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