Dimethyl Sulfone → 1-[4-Chloro-3,5-bis(methylamino)phenyl]-2-(methanesulfonyl)ethan-1-one

HRID 441319Notes

Reaction equation

[H-].[Na+].[CH3:3][S:4]([CH3:7])(=[O:6])=[O:5].[Cl:8][C:9]1[C:18]([N:19](C)[C:20](=O)C)=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][C:10]=1[N:24](C)[C:25](=O)C>CS(C)=O>[Cl:8][C:9]1[C:18]([NH:19][CH3:20])=[CH:17][C:12]([C:13](=[O:14])[CH2:3][S:4]([CH3:7])(=[O:6])=[O:5])=[CH:11][C:10]=1[NH:24][CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of 3.8 g. of sodium hydride (50% suspension in oil) and 11.2 g of dimethylsulfone in 40 ml. of dimethylsulfoxide was stirred with the exclusion of moisture for 2 hours at 50° C. 9.4 G. of methyl 4-chloro-3,5-bis-(N-methylacetamido)benzoate were then added, and the mixture was stirred at 80° C. for 3 hours. The solution was diluted with 200 ml. of ice water, the precipitated material extracted with ethyl acetate, the ethyl acetate solution purified over aluminum oxide, evaporated and the residue recrystallized from methanol, there being obtained 4'-chloro-3',5'-bis(methylamino)-2-methylsulfonylacetophenone having a melting point of 165°-167° C.

Workup

additionA suspension of 3.8 g
additionThe solution was diluted with 200 ml
extractionof ice water, the precipitated material extracted with ethyl acetate
customthe ethyl acetate solution purified over aluminum oxide
customevaporated
customthe residue recrystallized from methanol, there

Sources & evidence

ORD record: ord-f20a7ad5319d418098674fc81862db81
Source dataset: uspto-grants-1977_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04039543

Reaction notes

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