Methyl iodide → HCID 137227882, compound

HRID 1669383Notes

Reaction equation

HRID 1669383 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:25])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21]([NH:23][CH3:24])=[S:22].[H-].[Na+].I[CH3:29]>CN(C)C=O>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH3:9])[C:4](=[O:10])[C:3]=1[C:11](=[O:25])[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[N:23][CH3:24])[S:22][CH3:29]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136653811HCID 136653811, compound

Product 1

HCID 137227882HCID 137227882, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.40 g of 4-hydroxy-3-[3-[(3-methylthioureido)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone in 7 ml of dimethylformamide was added 0.044 g of sodium hydride (60% oily) at room temperature, and this was stirred for 1 hour. 0.26 g of iodomethane was added thereto, and this was stirred at room temperature overnight. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.079 g of yellow oily 4-hydroxy-3-[3-[(2,3-dimethylisothioureido)phenyl]-1-oxo-2-propenyl]-1,6-dimethyl-2(1H)-pyridinone [Compound No. (115a)].

Workup

  1. stirringthis was stirred at room temperature overnight
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8151695b7ef54e1086734bfeaa9e884e
Source dataset
uspto-grants-2011_08
Patent number
US07989478B2

Reaction notes

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