Hydroxyamine hydrochloride → 5-[(E)-C-[2-(2,5-dichlorophenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

HRID 1617944Notes

Reaction equation

HRID 1617944 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1)[CH2:10][C:11]([C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=O.Cl.[NH2:32][OH:33].C(=O)([O-])O.[Na+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:21]1[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:28])=[O:29])=[CH:25][CH:26]=1)[CH2:10]/[C:11](/[C:13]1[CH:14]=[CH:15][C:16](=[O:20])[N:17]([CH3:19])[CH:18]=1)=[N:32]\[OH:33]

Participants

4

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666689515-(3-(2,5-Dichlorophenyl)-3-(4-(methylsulfonyl)phenyl)propanoyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 580432695-[(E)-C-[2-(2,5-dichlorophenyl)-2-(4-methylsulfonylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Procedure

In analogy to example 151, step 3, 5-(3-(2,5-dichlorophenyl)-3-(4-(methylsulfonyl)-phenyl)propanoyl)-1-methylpyridin-2(1H)-one was reacted with hydroxylamine hydrochloride in the presence of sodium hydrogencarbonate to give the title compound containing 3% of the corresponding Z isomer as a colourless solid, MS (ESI+): m/z=479.1 [M+H]+.

Sources & evidence

ORD record
ord-31da338896c04e5f9d4666fa8fab05fa
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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