Dimethylformamide dimethyl acetal → N'-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]sulfonyl]-N,N-dimethylmethanimidamide
Reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([Cl:14])=[C:8]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:9]=1)(=[O:3])[CH3:2].CO[CH:17](OC)[N:18]([CH3:20])[CH3:19]>>[Cl:14][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH:2]=[CH:17][N:18]([CH3:20])[CH3:19])=[CH:9][C:8]=1[S:10]([N:13]=[CH:17][N:18]([CH3:20])[CH3:19])(=[O:12])=[O:11]Participants
3
Conditions
- Temperature
- -10 °C
Procedure
A mixture of 7.8 g (0.033 moles) of 5-acetyl 2-chlorobenzenesulfonamide [Chem. Abst., 63, 5563a (1965)] and 50 ml of N,N-dimethylformamide dimethyl acetal was refluxed for 5 hours, then cooled at -10° C. The precipitate formed was collected, washed with 50 ml of ether and air dried. The solid was boiled up in 400 ml of ethanol, treated with activated charcoal and filtered. The filtrate was cooled at -10° C. and filtered to collect an orange-red precipitate. The solid was washed with 50 ml of ethanol and dried in vacuo at 60° C. and gave 5.2 g of N'-[[2-chloro-5-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]sulfonyl]-N,N-dimethylmethanimidamide, mp 204°-206° C.
Workup
- temperaturewas refluxed for 5 hours
- customThe precipitate formed
- customwas collected
- washwashed with 50 ml of ether and air
- customdried
- additiontreated with activated charcoal
- filtrationfiltered
- temperatureThe filtrate was cooled at -10° C.
- filtrationfiltered
- customto collect an orange-red precipitate
- washThe solid was washed with 50 ml of ethanol
- customdried in vacuo at 60° C.
Sources & evidence
- ORD record
- ord-7521a81278a54388a88355fc4373b30f
- Source dataset
- uspto-grants-1986_04
- Patent number
- US04582833
Reaction notes
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