Dimethyl Sulfoxide → N-[2-(3,4-Dichlorophenyl)-4-oxobutyl]-N-methylbenzamide
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:31][CH2:32][OH:33])[CH2:20][N:21]([CH3:30])[C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:15]=[CH:16][C:17]=1[Cl:18].C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:13]=[C:14]([CH:19]([CH2:31][CH:32]=[O:33])[CH2:20][N:21]([CH3:30])[C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:15]=[CH:16][C:17]=1[Cl:18]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A solution of oxalyl chloride (878 mg) in dichloromethane (5 mL) was cooled to -78° C. and was treated dropwise with a solution of dimethyl sulfoxide (595 mg) in dichloromethane (2 mL). The resulting mixture was stirred at -78° C. for 15 minutes, and was treated dropwise with a solution of N-[2-(3,4-dichlorophenyl)-4-hydroxybutyl]-N-methylbenzamide (1.22 g) in dichloromethane (10 mL)/dimethyl sulfoxide (2 mL). The mixture was stirred at -78° C. for 1 hour, was treated with triethylamine (1.75 g), warmed to room temperature and stirred for 1 hour. The mixture was then poured into water and extracted with dichloromethane. The organic extract was washed (water, brine), dried, filtered through activated magnesium silicate [Florisil (trademark)] and evaporated to afford the aldehyde as a pale yellow oil (1.18 g); MS: m/z=350[(M+1), 35Cl2 ].
Workup
- stirringThe mixture was stirred at -78° C. for 1 hour
- temperaturewarmed to room temperature
- stirringstirred for 1 hour
- extractionextracted with dichloromethane
- extractionThe organic extract
- washwas washed (water, brine)
- customdried
- filtrationfiltered through activated magnesium silicate [Florisil (trademark)]
- customevaporated
Sources & evidence
- ORD record
- ord-cf3f575b46aa4e329a40bf1ab067bd9e
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05654299
Reaction notes
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