Water → HCID 70205299, compound

HRID 2393416Notes

Reaction equation

HRID 2393416 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.[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O.[H-].[Na+].O>CS(C)=O.C(O)(=O)C.CN(C)C=O>[Br:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[C:17]1[C:6]2[N:5]3[CH:1]=[CH:2][N:3]=[C:4]3[C:9](=[O:10])[NH:8][C:7]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]1=2

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 765833-BromobenzaldehydeHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 70205299HCID 70205299, compoundYield 16.9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 2.2 g of 5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one in 45 ml of anhydrous dimethyl sulphoxide, maintained under a nitrogen atmosphere and at a temperature in the region of 20° C., are added 2 g of 3-bromobenzaldehyde followed, over 5 minutes, by 0.72 g of 80% sodium hydride. The mixture is stirred for 15 hours at the same temperature, followed by slow addition of 45 ml of distilled water and 12 ml of acetic acid. The insoluble product formed is isolated by filtration, washed with distilled water and air-dried. The product obtained (3.1 g) is chromatographed on neutral silica gel, eluting with a dichloromethane/methanol mixture (90/10 by volume). The fractions containing the expected product are concentrated to dryness and the product obtained (1.9 g) is dissolved in a boiling mixture of 40 ml of acetic acid and 50 ml of dimethylformamide and, after cooling and storing for 15 hours at a temperature in the region of 5° C., the insoluble product formed is isolated by filtration, washed twice with 10 ml in total of acetic acid and twice with 10 ml in total of isopropyl ether and then dried under reduced pressure (1 mmHg; 0.13 kPa) at 80° C. 0.65 g of 10-(3-bromo-benzylidene)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained, melting at 340° C. (decomposition) (Analysis, % calculated C: 61.56, H: 3.10, Br: 20.48, N: 10.77, O: 4.10, % found C: 61.4, H: 3.2, N: 11.0).

Workup

  1. customThe insoluble product formed
  2. customis isolated by filtration
  3. washwashed with distilled water
  4. customair-dried
  5. customThe product obtained (3.1 g)
  6. customis chromatographed on neutral silica gel
  7. washeluting with a dichloromethane/methanol mixture (90/10 by volume)
  8. additionThe fractions containing the expected product
  9. concentrationare concentrated to dryness
  10. customthe product obtained (1.9 g)
  11. temperatureafter cooling
  12. waitstoring for 15 hours at a temperature in the region of 5° C.
  13. customthe insoluble product formed
  14. customis isolated by filtration
  15. washwashed twice with 10 ml in total of acetic acid and twice with 10 ml in total of isopropyl ether
  16. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 80° C

Sources & evidence

ORD record
ord-1f433a931d14470faa9d016deca3c805
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

Loading…