Potassium Cyanide → 6-(4-cyanophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one
Reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C-:22]#[N:23].[K+]>O>[C:22]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[NH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)#[N:23]Participants
Procedure
In the same manner as Example 18-(1), there was produced a solution containing the diazonium salt derived from 6-(4-aminophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (3.06 g). The solution was neutralized carefully with saturated aqueous sodium carbonate followed by addition of an ice-cooled solution of potassium cyanide (1.88 g) and cuprous cyanide (1.17 g) in water (12 ml). The mixture was stirred for an hour and the crystals which formed were recovered by filtration, washed with water, 1N aqueous sodium hydroxide, 1N hydrochloric acid and water in that order and dissolved in aqueous ethanol. The solution was treated with activated carbon and concentrated to dryness under reduced pressure. The residue was purified by silica gel (190 g) column chromatography [eluent: chloroform-methanol (20:1)] to give 6-(4-cyanophenyl)-5-methyl-4,5-dihydro-1,2,4-triazin-3(2H)-one (1.469 g).
Workup
- customthe crystals which formed
- filtrationwere recovered by filtration
- washwashed with water, 1N aqueous sodium hydroxide, 1N hydrochloric acid and water in that order
- dissolutiondissolved in aqueous ethanol
- additionThe solution was treated with activated carbon
- concentrationconcentrated to dryness under reduced pressure
- customThe residue was purified by silica gel (190 g) column chromatography [eluent: chloroform-methanol (20:1)]
Sources & evidence
- ORD record
- ord-73be7d759b06450496f84fd0f55fa05d
- Source dataset
- uspto-grants-1986_10
- Patent number
- US04618610
Reaction notes
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