Allylamine → N-allyl-N'-(2-hydroxy-1,1-dimethylethyl)urea
Reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(N(CC)CC)C.Cl[C:13](OC1C=CC([N+]([O-])=O)=CC=1)=[O:14].[NH2:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28]>C(Cl)(Cl)Cl>[CH2:1]([NH:4][C:13]([NH:25][C:26]([CH3:30])([CH3:29])[CH2:27][OH:28])=[O:14])[CH:2]=[CH2:3]Participants
6
Procedure
To a chloroform solution (60 mL) of allylamine (1.5 g, 26.3 mmol) were added triethylamine (4.9 mL, 35.5 mmol) and at 4° C. 4-nitrophenyl chloroformate (6.09 g, 30.2 mmol), and the mixture was stirred for an hour. To this reaction solution was added at the same temperature a chloroform solution (3 mL) of 2-amino-2-methylpropanol (2.58 g, 28.9 mmol), and the mixture was stirred overnight at room temperature. The reaction solvent was evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (ethyl acetate) to obtain the title compound (4.0 g, 88%) as a yellow oily compound.
Workup
- customat 4° C
- customThe reaction solvent was evaporated under reduced pressure
- customThus obtained residue was purified with silica gel column chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-4f1d6c1419f74566b338a9a777d5d4f9
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973012B2
Reaction notes
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