Potassium Carbonate → 5-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-(2-methoxyethyl)pyridin-2-one

HRID 1617922Notes

Reaction equation

HRID 1617922 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:18])[NH:16][CH:17]=2)=O)=[C:4]([CH3:29])[CH:3]=1.Br[CH2:31][CH2:32][O:33][CH3:34].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:42][OH:43].C(=O)([O-])O.[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=2)[CH2:9]/[C:10](/[C:12]2[CH:13]=[CH:14][C:15](=[O:18])[N:16]([CH2:31][CH2:32][O:33][CH3:34])[CH:17]=2)=[N:42]\[OH:43])=[C:4]([CH3:29])[CH:3]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 670157545-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)pyridin-2(1H)-one

Product 1

HCID 580432335-[(E)-C-[2-(4-chloro-2-methylphenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-(2-methoxyethyl)pyridin-2-one

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

In analogy to example 161, step 1, 5-(3-(4-chloro-2-methylphenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)pyridin-2(1H)-one (example 339, step 2) was reacted with 1-bromo-2-methoxyethane in the presence of potassium carbonate and a catalytic amount of tetrabutylammonium iodide. The product of this reaction was reacted in analogy to example 151, step 3, with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound as a colourless solid containing less than 10% of the corresponding Z isomer, MS (ESI+): m/z=503.2 [M+H]+.

Sources & evidence

ORD record
ord-f3ce9f4dbed045b48f984fc03aa87d1f
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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