HCID 1472320, compound → HCID 22905781, compound
Reaction equation
[BH4-].[Na+].[C:3]([C:5]1[CH:17]=[CH:16][C:8]([CH:9]=[N:10][N:11]2[CH:15]=[N:14][N:13]=[CH:12]2)=[CH:7][CH:6]=1)#[N:4]>CO>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][NH:10][N:11]2[CH:12]=[N:13][N:14]=[CH:15]2)=[CH:16][CH:17]=1)#[N:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2.28 Grams of sodium borohydride was added gradually to a suspension of 9.85 g of 4-[(4-cyanobenzylidene)amino]-4H-1,2,4-triazole obtained in Referential Example 1 in 100 ml methanol under ice-cooling. The reaction mixture was stirred at the same temperature for 1 hour, and the solvent was removed by distillation under reduced pressure. Water and sodium chloride were added to the residue successively for salting-out, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was subjected to silica gel column chromatography, and crude crystals from the chloroform/methanol (15:1) eluate were washed with chloroform to give 4.2 g of 4-[(4-cyanobenzyl)amino]-4H-1,2,4-triazole.
Workup
- temperaturecooling
- customthe solvent was removed by distillation under reduced pressure
- additionWater and sodium chloride were added to the residue successively for salting-out
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was removed by distillation under reduced pressure
- washcrude crystals from the chloroform/methanol (15:1) eluate were washed with chloroform
Sources & evidence
- ORD record
- ord-e30c5372ef654b3a87b8811688fd2599
- Source dataset
- uspto-grants-1997_10
- Patent number
- US05674886
Reaction notes
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