Hydrochloric Acid → N-(2-furanylmethyl)2-fluoro-5-nitrobenzamide
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH2:14]([NH2:20])[C:15]1[O:19][CH:18]=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1.Cl>C1COCC1>[O:19]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:14][NH:20][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:2]=1[F:1]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Procedure
To a 0.2M solution of 2-fluoro-5-nitrobenzoic acid (1.0 g, 5.4 mmol, Aldrich) in anhydrous THF at ambient temperature was added furfurylamine (1.1 g, 5.9 mmol), HBTU (2.24 g g, 5.9 mmol, Chem-Impex), HOBT (0.8 g, 5.9 mmol, Novabiochem) and NMM (0.59 mL, 5.4 mmol, Aldrich). The resulting solution was stirred for 18 hr. To the reaction mixture was added a 1M solution of aqueous hydrochloric acid (30 mL). The crude mixture was extracted 3× with EtOAc (50 mL). The organic layers were combined, washed one time with a saturated aqueous solution of NaHCO3 (100 mL), one time with brine (100 mL), dried over Na2SO4, and concentrated under vacuum to yield 1.4 g (100%) of product as an off white solid which was used without further purification.
Workup
- extractionThe crude mixture was extracted 3× with EtOAc (50 mL)
- washwashed one time with a saturated aqueous solution of NaHCO3 (100 mL), one time with brine (100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-4d3d4949ff844129acddf107d638b5fa
- Source dataset
- uspto-grants-2008_10
- Patent number
- US07439242B2
Reaction notes
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