Acetamide, N-[(dimethylamino)methylidene]- → N-[(E)-[(2-bromo-5-fluorophenyl)hydrazinylidene]methyl]acetamide
Reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[NH:10][NH2:11].CN([CH:15]=[N:16][C:17](=[O:19])[CH3:18])C>C1COCC1.CC(O)=O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[NH:10]/[N:11]=[CH:15]/[NH:16][C:17](=[O:19])[CH3:18]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Alternatively, to a mixture of (2-bromo-5-fluoro-phenyl)-hydrazine hydrochloride (5.9 g, 28.8 mmol) and N-((dimethylamino)methylene)acetamide (3.30 g, 28.8 mmol) in THF (30 mL) was added 5 drops of HOAc, and the mixture stirred at room temperature under nitrogen for 15 min. The mixture was concentrated in vacuo, and the residue suspended in a mixture of ether (50 mL) and hexanes (50 mL) and the resulting precipitate collected and air-dried to provide 5.7 g of the title compound as an off-white powder. A second crop gave an additional 0.3 g.
Workup
- concentrationThe mixture was concentrated in vacuo
- additionthe residue suspended in a mixture of ether (50 mL) and hexanes (50 mL)
- customthe resulting precipitate collected
- customair-dried
Sources & evidence
- ORD record
- ord-6363612bd71b49dbb79a559ffe5ae706
- Source dataset
- uspto-grants-2011_10
- Patent number
- US08039458B2
Reaction notes
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