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

HRID 1290747
Notes
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Reaction equation

HRID 1290747 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.[H-].[Na+].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>CS(C)=O.C(O)(=O)C>[CH2:20]([C:17]1([CH2:7][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[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)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydride2×HCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 1891817310,10-dibenzyl-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Solvent
HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 0.45 g of 5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one in 20 ml of dimethyl sulphoxide under nitrogen are added, at a temperature in the region of 20° C. and with stirring, 60 mg of sodium hydride. The stirring is continued for 2 hours and a further 66 mg of sodium hydride are then added. The reaction medium is heated to 45° C. for 30 minutes, cooled to 20° C. and 0.25 ml of benzyl bromide are added. After continuing the stirring for 3 hours, the reaction mixture is poured into 150 ml of water, acidified to pH 4 with acetic acid and extracted with three times 60 ml of chloroform. The organic phases are combined, washed with twice 100 ml of water, dried over magnesium sulphate, filtered and concentrated on a rotary evaporator. The black solid obtained (0.78 g) is purified by chromatography on a column of silica (70 g) with a mixture of dichloromethane and methanol (95/5 by volume) to give 0.1 g of 10,10-dibenzyl-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one in the form of a pale green solid melting above 260° C. [N.M.R. spectrum: (200 MHz; DMSO d6 ; δ in ppm): 3.63 and 3.85 (2d, J=14 Hz, 2H each: --CH2 --Ar); 6.36 (d, J=7 Hz, 4H: ortho-H of the benzyls); from 6.75 to 6.95 (mt, 6H: meta-H and para-H of the benzyls); from 7.29 to 7.45 (2t, J=7.5 Hz, 1H each: --H7 and --H8); 7.82 and 8.80 (2s broad, 1H each: --H of the imidazole); 7.38 and 8.02 (2d, J=7.5 Hz, 1H each: --H6 and --H9); 11.9 (cplx, 1H: --NH--)].

Workup

  1. temperaturecooled to 20° C.
  2. customstirring for 3 hours
  3. extractionextracted with three times 60 ml of chloroform
  4. washwashed with twice 100 ml of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated on a rotary evaporator
  8. customThe black solid obtained (0.78 g)
  9. customis purified by chromatography on a column of silica (70 g) with a mixture of dichloromethane and methanol (95/5 by volume)

Sources & evidence

ORD record
ord-aa1c22c1b9104fff84db1150161cdc98
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753657

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes