1-Methyl-N5-[3-[3-[(dimethylamino)methyl]phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine → 1-methyl-N-[3-[3-(N,N-dimethylaminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-5-amine
Reaction equation
N([O-])=O.[Na+].[CH3:5][N:6]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]([CH3:25])[CH3:24])[CH:17]=2)=[N:9][C:8](N)=[N:7]1>O.S(=O)(=O)(O)O.C(O)C.[Cl-].[Na+].O>[CH3:5][N:6]1[C:10]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]([CH3:24])[CH3:25])[CH:17]=2)=[N:9][CH:8]=[N:7]1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Procedure
A solution of sodium nitrite (1.74 g) in water (15 ml) was added dropwise to a solution of 1-methyl-N5 -[3-[3-(N,N-dimethylaminomethyl)phenoxy]propyl]-1H-1,2,4-triazole-3,5-diamine (5 g) in concentrated sulphuric acid (3.68 g) and ethanol (200 ml). The reaction mixture was heated at 65° for 4 h, cooled, treated with saturated brine (100 ml) and extracted with ethyl acetate. Evaporation of the organic extract gave a red oil which was extracted with ether. Distillation of the ether extracts gave the title compound as a pale yellow oil (1.8 g) b.p. 190° (0.04 mm). tlc System A,Rg 0.6.
Workup
- temperatureThe reaction mixture was heated at 65° for 4 h
- temperaturecooled
- extractionextracted with ethyl acetate
- customEvaporation of the
- extractionorganic extract
- customgave a red oil which
- extractionwas extracted with ether
- distillationDistillation of the ether extracts
Sources & evidence
- ORD record
- ord-16e83c10004c4294ab3285cb453aad91
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04536508
Reaction notes
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