Dimethyl Sulfoxide → 1-[2,4-Bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carbaldehyde
Reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]([F:35])([F:34])[C:13]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[CH2:22][CH2:21][CH:20]([CH2:23][OH:24])[CH2:19][CH2:18][C:17]1=[O:25].[Cl-].[NH4+]>ClCCl.C(N(CC)CC)C>[F:35][C:12]([F:11])([F:34])[C:13]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[C:17](=[O:25])[CH2:18][CH2:19][CH:20]([CH:23]=[O:24])[CH2:21][CH2:22]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of DMSO (1.40 g) in dichloromethane (100 mL) was slowly added a solution of oxalyl chloride (2.48 g) in dichloromethane (200 mL) at −78° C. The reaction mixture was stirred for 5 min, a solution of 1-[2,4-bis(trifluoromethyl)benzyl]-5-(hydroxymethyl)azepan-2-one (6.0 g) in dichloromethane (100 mL) was added dropwise, and the mixture was stirred for 15 min. Triethylamine (8.2 g) was added and the mixture was allowed to warm to room temperature. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether) to give the title compound (2.76 g).
Workup
- stirringthe mixture was stirred for 15 min
- extractionthe mixture was extracted with ethyl acetate
- dry with materialThe extract was dried over anhydrous sodium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/petroleum ether)
Sources & evidence
- ORD record
- ord-fe932f345f2d47a3bc7fd82c2e807935
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772277B2
Reaction notes
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