Methane → 10-benzamido-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one

HRID 1290761Notes

Reaction equation

HRID 1290761 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:11][CH:12]1[C:24]2[N:23]3[CH:25]=[CH:26][N:27]=[C:22]3[C:21](=[O:28])[NH:20][C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2.C>[OH-].[Na+].CS(C)=O>[C:1]([NH:11][CH:12]1[C:24]2[N:23]3[CH:25]=[CH:26][N:27]=[C:22]3[C:21](=[O:28])[NH:20][C:19]=2[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 7412Benzoyl chlorideHCID 1897547210-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride

Product 1

HCID 1891818410-benzamido-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-oneYield 45.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
20 °C

Procedure

1.7 g of benzoyl chloride are added over 1 minute to a solution of 3.1 g of 10-amino-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride in 200 ml of 0.1N sodium hydroxide. The mixture is stirred for 2 hours at a temperature in the region of 20° C. and the insoluble material is separated out by filtration, washed twice with 200 ml in total of distilled water and air-dried. The product obtained (3 g) is dissolved in 100 ml of dimethyl sulphoxide and, after addition of decolorizing charcoal, the solution is filtered. The filter is washed with 20 ml of dimethyl sulphoxide and the filtrate and the washings are then combined and 80 ml of distilled water are added at 20° C. The insoluble material is separated out by filtration, washed twice with 50 ml in total of distilled water and with 25 ml of acetone and then dried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C. 1.75 g of 10-benzamido-5H,10H-imidazo[1,2-a]-indeno[1,2-e]pyrazin-4-one are thus obtained, decomposing without melting at 300° C. [N.M.R. spectrum: (200 MHz; DMSO d6 ; δ in ppm): 6.40 (d, J=8.5 Hz, 1H: CH--N); from 7.30 to 7.70 (mt, 8H: --H6, --H7, --H8, --H9, aromatic --H para and meta to the --CO--NH-- and --H of the imidazole); from 7.80 to 8.00 (mt, 3H: aromatic --H ortho to the --CO--NH-- and --H of the imidazole); 9.14 (d, J=8.5 Hz, 1H: --NH--); 12.55 (cplx, 1H: --CO--NH-- of the ring)].

Workup

  1. customthe insoluble material is separated out by filtration
  2. washwashed twice with 200 ml in total of distilled water
  3. customair-dried
  4. customThe product obtained (3 g)
  5. filtrationthe solution is filtered
  6. washThe filter is washed with 20 ml of dimethyl sulphoxide
  7. addition80 ml of distilled water are added at 20° C
  8. customThe insoluble material is separated out by filtration
  9. washwashed twice with 50 ml in total of distilled water and with 25 ml of acetone
  10. customdried under reduced pressure (1 mmHg; 0.13 kPa) at 100° C

Sources & evidence

ORD record
ord-a556a89a75644307a0bdf6c777496d8e
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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