Dimethyl Sulfoxide → HCID 67015252, compound

HRID 1290763Notes

Reaction equation

HRID 1290763 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.[H-].[Na+].[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH:34]=O)=[CH:26][CH:25]=1>C(O)(=O)C.O>[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH:34]=[C:17]2[C:6]3[N:5]4[CH:1]=[CH:2][N:3]=[C:4]4[C:9](=[O:10])[NH:8][C:7]=3[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]2=3)=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 780724-QuinolinecarboxaldehydeHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 67015252HCID 67015252, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

The procedure is performed as in Example 28, but starting with 3 g of 5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one, 60 ml of dimethyl sulphoxide, 0.96 g of 80% sodium hydride and 3.18 g of 4-quinolincarboxaldehyde. After treating with water and acetic acid, the suspension obtained is filtered and the solid thus isolated is washed with 2×30 ml of water and then 4×30 ml of acetone and dried at 100° C. under vacuum (2 mmHg; 0.26 kPa). 3.9 g of 10-(4-quinolylmethylene)-5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one are obtained, in the form of an orange solid melting above 260° C. (Analysis % calculated C: 76.23, H: 3.89, N: 15.46, O: 4.41, % found C: 75.9, H: 4.2, N: 15.4).

Workup

  1. customthe suspension obtained
  2. filtrationis filtered
  3. customthe solid thus isolated
  4. washis washed with 2×30 ml of water
  5. dry with material4×30 ml of acetone and dried at 100° C. under vacuum (2 mmHg; 0.26 kPa)

Sources & evidence

ORD record
ord-cd20c1a48e784282aab49739cee6b0e1
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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