Triethylamine → N,N-diisopropyl-N'-(2-dimethylaminoethyl)-N'-(4,6-dimethyl-2-pyridyl)urea
Reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=1.C(N(CC)CC)C.[CH:22]([N:25]([CH:29]([CH3:31])[CH3:30])[C:26](Cl)=[O:27])([CH3:24])[CH3:23]>C1C=CC=CC=1>[CH:22]([N:25]([CH:29]([CH3:31])[CH3:30])[C:26]([N:5]([CH2:4][CH2:3][N:2]([CH3:14])[CH3:1])[C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:27])([CH3:24])[CH3:23]Participants
5
Procedure
A solution of 5.80 g (30.0 mmoles) of 2-(2-dimethylaminoethylamino)-4,6-dimethylpyridine (from Example 1, B) and 2.20 ml (30.0 mmoles) of triethylamine in 50 ml of benzene is dried by azeotropic distillation. After adding 4.91 g (30.0 mmoles) of diisopropylcarbamoyl chloride, the reaction mixture is heated at reflux for 24 hours. The crude product, after removal of solvent, is chromatographed on silica gel using 5% methanol in chloroform as eluant. Appropriate fractions are combined, the solvent removed and product distilled through a short path still to give 2.32 g (24.1% yield) of N,N-diisopropyl-N'-(2-dimethylaminoethyl)-N'-(4,6-dimethyl-2-pyridyl)urea as a colorless oil boiling at 148°/0.35 mm.
Workup
- temperaturethe reaction mixture is heated
- temperatureat reflux for 24 hours
- customThe crude product, after removal of solvent
- customis chromatographed on silica gel using 5% methanol in chloroform as eluant
- customthe solvent removed
- distillationproduct distilled through a short path still
Sources & evidence
- ORD record
- ord-a5096b23f98e4f66bd17520b4d42d039
- Source dataset
- uspto-grants-1980_05
- Patent number
- US04203988
Reaction notes
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