Methyl iodide → HCID 20268267, compound

HRID 1719431Notes

Reaction equation

HRID 1719431 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[C:24](=[O:26])[CH3:25])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27]I.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=2[C:24](=[O:26])[CH3:25])[CH3:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 13371473HCID 13371473, compound

Product 1

HCID 20268267HCID 20268267, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[II; R=5-CH3O, R'=CH3, R"=H, OR°=4-OCH2C6H5, Alk=CH3 ] is obtainable by N-alkylation of 1-[2-(4-benzyloxyphenylamino)-5-methoxyphenyl]ethanone (Example 1b) with methyl iodide in the presence of sodium hydride. A preferred procedure is to add slowly methyl iodide in excess to a cooled (0° C.) suspension of starting material and sodium hydride in an inert solvent, e.g. dimethylformamide, and stirring the reaction mixture at ambient temperature until the reaction is complete.

Workup

  1. temperaturea cooled

Sources & evidence

ORD record
ord-a7688f66d4c1468faf46248f286a03ac
Source dataset
uspto-grants-1985_09
Patent number
US04539429

Reaction notes

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