2,4-Difluoroaniline → HCID 9971553, compound
Reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:24]=1[NH2:25].[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36](O)=[O:37]>CN(C=O)C>[Br:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([NH:25][C:24]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=1[F:22])=[O:37]Participants
Procedure
WSC (2.1 g, 11 mmols) and HOBt (1.49 g, 11 mmols) were added to a DMF (30 ml) solution of 2,4-difluoroaniline (1.29 g, 10 mmols) and 5-bromopentanoic acid (2.7 g, 15 mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with ether. The organic layer was washed with water, 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and satiated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. Then, the residue was purified through preparative thin-layer chromatography (developer:hexane/acetone=5/1), and the resulting crystals were recrystallized from ether-hexane to obtain 2.0 g (yield: 68%) of 5-bromo-N-(2,4-difluorophenyl)pentanamide as colorless needle-like crystals.
Workup
- extractionThe reaction mixture was extracted with ether
- washThe organic layer was washed with water, 1 N HCl
- dry with materialdried with anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThen, the residue was purified through preparative thin-layer chromatography (developer:hexane/acetone=5/1)
- customthe resulting crystals were recrystallized from ether-hexane
Sources & evidence
- ORD record
- ord-71c91a5ac3204c169f03f7d575fb7a64
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825223B2
Reaction notes
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