Methyl iodide → 2-[2,4-Dichloro-5-(1-methylethoxy)phenyl]-4,6-dimethyl-1,2,4-triazine-3,5(2H,4H)-dione

HRID 1164753Notes

Reaction equation

HRID 1164753 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:18](=[O:19])[NH:17][C:16](=[O:20])[C:15]([CH3:21])=[N:14]1.[H-].[Na+].I[CH3:25]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[N:13]1[C:18](=[O:19])[N:17]([CH3:25])[C:16](=[O:20])[C:15]([CH3:21])=[N:14]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 142769432-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione

Product 1

HCID 147478302-[2,4-Dichloro-5-(1-methylethoxy)phenyl]-4,6-dimethyl-1,2,4-triazine-3,5(2H,4H)-dioneYield 64.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a manner similar to Example III, Step G, the reaction of 0.28 g (0.00085 mole) of 2-[2,4-dichloro-5-(1-methylethoxy)phenyl]-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione with 0.037 g (0.00093 mole) of sodium hydride (60% in oil) and 0.13 g (0.00093 mole) of iodomethane in 10 mL of N,N-dimethylformamide produced 0.19 g of 2-[2,4-dichloro-5-(1-methylethoxy)phenyl]-4,6-dimethyl-1,2,4-triazine-3,5(2H,4H)-dione as a low melting solid, Compound 13 in the tables.

Sources & evidence

ORD record
ord-c51a8e7c133f4302acb9f4eb0472cd07
Source dataset
uspto-grants-1990_03
Patent number
US04906286

Reaction notes

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