O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → N-(4-Chloro-3-nitrobenzyl)-1-(trifluoromethyl)cyclopropanecarboxamide
Reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1([C:6](O)=[O:7])[CH2:5][CH2:4]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH2:42])=[CH:37][C:36]=1[N+:43]([O-:45])=[O:44]>CN(C=O)C>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][NH:42][C:6]([C:3]2([C:2]([F:10])([F:9])[F:1])[CH2:5][CH2:4]2)=[O:7])=[CH:37][C:36]=1[N+:43]([O-:45])=[O:44]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
TEA (21.7 mL; 156 mmol) was added to a mixture of 1-(trifluoromethyl)-cyclopropanecarboxylic acid (8.00 g; 51.9 mmol) and TBTU (16.7 g; 52 mmol) in DMF (40 mL). After 1 h at rt, a solution of (4-chloro-3-nitrophenyl)methylamine hydrochloride (11.6 g; 52 mmol) in DMF (70 mL) was added dropwise over 30 min. After 17 h at rt, the mixture was concentrated and the residue partitioned between water and MTBE. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was purified by column chromatography to give the sub-title compound. Yield: 13.191 g (78%).
Workup
- waitAfter 17 h at rt
- concentrationthe mixture was concentrated
- customthe residue partitioned between water and MTBE
- washThe organic layer was washed with water
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-3606a1ef0a06425e92d71fdd30d73eb0
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921405B2
Reaction notes
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