Butylamine → Triazbutil
Reaction equation
[C-:1]#[N:2].[CH2:3]([NH3+:7])[CH2:4][CH2:5][CH3:6].NN.[CH2:10]([NH2:14])CCC>>[CH2:3]([N:7]1[CH:10]=[N:14][N:2]=[CH:1]1)[CH2:4][CH2:5][CH3:6]Participants
4
Conditions
- Temperature
- 75 °C
Procedure
In Example 6, Example 5 was repeated except that the butylamine-HCN mixture was not heated so as to avoid polymerizing the hydrogen cyanide. An NMR spectrum of this mixture gave no evidence of butylformamidine formation but rather was consistent with a simple solution of butylammonium cyanide in butylamine. Hydrazine was added and the reaction mixture was heated to 75° C. to give a 63% yield of 4-n-butyl-1,2,4-triazole in only four hours. The only differences between this experiment and Examples 3 and 4 were the order of the HCN--H2NNH2 additions and the amount of NH4Cl catalyst used; the former seems to have had no discernible effect while the latter is presumably responsible for the significant rate increase.
Sources & evidence
- ORD record
- ord-2d4ac58b85c9496ab0a21cd2bf5fe368
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04238617
Reaction notes
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