alpha-Chloro-2-methyl-3-nitrotoluene → 4-(isobutylthio)-1-(2-methyl-3-nitrobenzyl)pyridine-2(1H)-one

HRID 1009182Notes

Reaction equation

HRID 1009182 reaction equation
[CH2:1]([S:5][C:6]1[CH:11]=[CH:10][NH:9][C:8](=[O:12])[CH:7]=1)[CH:2]([CH3:4])[CH3:3].CC([O-])(C)C.[K+].[CH3:19][C:20]1[C:27]([N+:28]([O-:30])=[O:29])=[CH:26][CH:25]=[CH:24][C:21]=1[CH2:22]Cl>CN(C=O)C>[CH2:1]([S:5][C:6]1[CH:11]=[CH:10][N:9]([CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[C:27]([N+:28]([O-:30])=[O:29])[C:20]=2[CH3:19])[C:8](=[O:12])[CH:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 108947alpha-Chloro-2-methyl-3-nitrotolueneHCID 140726754-Isobutylthio-2-pyridoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 673052004-(isobutylthio)-1-(2-methyl-3-nitrobenzyl)pyridine-2(1H)-oneYield 49.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 100 mg of 4-(isobutylthio)pyridine-2(1H)-one, 2 ml of DMF, 65 mg of t-BuOK was stirred at room temperature and 105 mg of 2-methyl-3-nitrobenzyl chloride was added. After 3 hour, the resulting solution was evaporated, extracted with dichloromethane and subjected to silica gel column chromatography (hexane/ethyl acetate) to obtain the compound (90 mg).

Workup

  1. customthe resulting solution was evaporated
  2. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-035691ddf2b44c0e80f2cc66877af594
Source dataset
uspto-grants-2011_07
Patent number
US07973060B2

Reaction notes

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