Reaction equation
[N+]([O-])(O)=O.[CH2:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[NH2:19])[CH:6]=[CH2:7].[N:20]#[C:21][NH2:22].N>C(O)C.O>[CH2:5]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[NH:19][C:21]([NH2:22])=[NH:20])[CH:6]=[CH2:7]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Nitric acid (1.04 mL of 65%, 15 mmol) is added to a stirred solution of 2-[(2-propenyloxy)-methyl]-5-nitrobenzenamine (3.15 g, 15 mmol) in ethanol (30 mL) at 200C. A solution of cyanamide (0.95 g, 22.5 mmol) in water (1 mL) is then added dropwise to the stirred mixture at 95° C. over a period of 60 min. The mixture is heated at 95° C. for 14 h, with additional aliquots of cyanamide (total 2.2 g, 58 mmol) being added throughout this period and with the acidity being periodically adjusted to pH 3 by the addition of nitric acid (65%). The resulting mixture is cooled to 0° C., basified with aqueous ammonia (5 mL of 25%), diluted with water (150 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts are washed with saturated aqueous ammonium chloride (50 mL), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to give the title compound as a brown oil, which is used directly in the next step without further purification.
Workup
- additionbeing added throughout this period and with the acidity
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined extracts are washed with saturated aqueous ammonium chloride (50 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent is evaporated off under reduced pressure
Sources & evidence
- ORD record
- ord-e94eaa7fee594f4b821665c3efa7ee49
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557105B2
Linked notes
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