Water → 10-acetamido-10-benzyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

HRID 2393417Notes

Reaction equation

HRID 2393417 reaction equation
[C:1]([NH:4][CH:5]1[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)(=[O:3])[CH3:2].[H-].[Na+].[CH2:24](Cl)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CS(C)=O.C(O)(=O)C>[C:1]([NH:4][C:5]1([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]2[N:16]3[CH:18]=[CH:19][N:20]=[C:15]3[C:14](=[O:21])[NH:13][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 1529136110-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 1897548410-acetamido-10-benzyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-oneYield 28.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
20 °C

Procedure

To a suspension of 1.4 g of 10-acetamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one in 35 ml of anhydrous dimethyl sulphoxide, maintained at 20° C. under a nitrogen atmosphere, is added 0.36 g of 80% sodium hydride and the mixture is stirred for 20 minutes. A solution of 0.7 g of benzyl chloride in 1 ml of anhydrous dimethyl sulphoxide is then added dropwise over 5 minutes at the same temperature and, after stirring for 3 hours, the reaction mixture is poured into a mixture of 200 ml of distilled water, 80 g of ice and 6 ml of acetic acid. The insoluble material formed is removed by centrifugation and the supernatant solution is stored for 15 hours at a temperature in the region of 20° C. The insoluble product formed is isolated by filtration, washed twice with 10 ml in total of distilled water and with 5 ml of acetone, and then dried under reduced pressure (1 mmHg; 0.13 kPa) at 80° C. 0.52 g of 10-acetamido-10-benzyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one is thus obtained, melting at 325° C. (decomposition) (Analysis, % calculated C: 71.34, H: 4.90, N: 15.13, O: 8.64, % found C: 71.2, H: 4.5, N: 15.0).

Workup

  1. stirringafter stirring for 3 hours
  2. customThe insoluble material formed
  3. customis removed by centrifugation
  4. waitthe supernatant solution is stored for 15 hours at a temperature in the region of 20° C
  5. customThe insoluble product formed
  6. customis isolated by filtration
  7. washwashed twice with 10 ml in total of distilled water and with 5 ml of acetone
  8. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 80° C

Sources & evidence

ORD record
ord-6bfb6534c9da49c7935ebc3152339ee7
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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