Diisopropylethylamine → N-(2,4-dichlorophenethyl)-2-fluoro-4-hydroxybenzamide
Reaction equation
[F:1][C:2]1[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][CH2:54][NH2:55]>CN(C=O)C>[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][CH2:54][NH:55][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:2]=1[F:1]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-fluoro-4-hydroxybenzoic acid (200 mg, 1.28 mmol) in DMF (3 ml) at ambient temperature were added HATU (536 mg, 1.41 mmol) and DIEA (268 μL, 1.54 mmol). The reaction was stirred for 30 minutes and then 2-(2,4-dichlorophenyl)ethanamine (193 μL, 1.28 mmol) was added. The reaction was stirred overnight, then concentrated and diluted with water and dichloromethane. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with brine and dried over MgSO4. The crude product was purified by silica gel chromatography) to give N-(2,4-dichlorophenethyl)-2-fluoro-4-hydroxybenzamide (0.420 g).
Workup
- stirringThe reaction was stirred overnight
- concentrationconcentrated
- additiondiluted with water and dichloromethane
- extractionThe aqueous layer was extracted with dichloromethane
- washthe combined organic layers were washed with brine
- dry with materialdried over MgSO4
- customThe crude product was purified by silica gel chromatography)
Sources & evidence
- ORD record
- ord-475e1f3892c340aca8aff879ad481cb8
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08183289B2
Reaction notes
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