1-Hydroxybenzotriazole → HCID 14517193, compound
Reaction equation
[CH3:1][C:2]1[NH:3][C:4]([CH3:10])=[C:5]([C:7](O)=[O:8])[N:6]=1.Cl.C([N:14]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH3:1][C:2]1[NH:3][C:4]([CH3:10])=[C:5]([C:7]([NH2:14])=[O:8])[N:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2,5-dimethyl-4-imidazolecarboxylic acid (1.4 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.93 g), and N-hydroxybenzotriazole (1.49 g) in N,N-dimethylformamide (14 ml) was stirred at 0° C. for 15 minutes. A solution of (2E,4E)- and (2Z,4E)-4-methyl-2,4-heptadien-1-ylamine (1.79 g) in N,N-dimethylformamide (6 ml) was added dropwise to the solution over a period of 10 minutes. The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 24 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (3% methanol-chloroform) to give N-[(2E,4E)- and (2Z,4E)-4-methyl-2,4-heptadien-1-yl]-2,5-dimethyl-4-imidazolecarboxamide (1.6 g) as an oil.
Workup
- waitat room temperature for 24 hours
- extractionextracted twice with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated in vacuo
- customThe residue was chromatographed on silica gel (3% methanol-chloroform)
Sources & evidence
- ORD record
- ord-d9a72f38c19a4c778624bf78ed64520d
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05691366
Reaction notes
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