Dimethylformamide dimethyl acetal → N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethyl-4-methylbenzenesulfonamide
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:21][CH3:22])[S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2].CO[CH:25](OC)[N:26]([CH3:28])[CH3:27]>>[CH3:25][N:26]([CH3:28])[CH:27]=[CH:2][C:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:21][CH3:22])[S:11]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)=[O:3]Participants
3
Conditions
- Temperature
- -10 °C
Procedure
A 31.2 g portion of N-(3-acetylphenyl)-N-ethyl-4-methylbenzenesulfonamide and 50 ml of dimethylformamide dimethylacetal were combined and stirred on a steam bath for 18 hours, then evaporated in vacuo to an oil. This oil was triturated with hexane at -10° C. The hexane was decanted and the residue dissolved in 125 ml of boiling dichloromethane and then filtered. The filtrate was reheated to boiling, 200 ml of hexane was added and the mixture cooled to -10° C. The precipitate was collected, washed with hexane and dried, giving 21.6 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethyl-4-methylbenzenesulfonamide.
Workup
- customevaporated in vacuo to an oil
- customThis oil was triturated with hexane at -10° C
- customThe hexane was decanted
- dissolutionthe residue dissolved in 125 ml of boiling dichloromethane
- filtrationfiltered
- addition200 ml of hexane was added
- customThe precipitate was collected
- washwashed with hexane
- customdried
Sources & evidence
- ORD record
- ord-aaa7e6a1ab4f4dac94364ef9e88eab45
- Source dataset
- uspto-grants-1985_06
- Patent number
- US04521422
Reaction notes
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