Methyl iodide → N-(2,4-Dichloro-5-methoxyphenyl)acetamide

HRID 846501Notes

Reaction equation

HRID 846501 reaction equation
[CH3:1][C:2]([NH:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[C:7]([OH:13])[CH:6]=1)=[O:3].[C:14](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[CH3:1][C:2]([NH:4][C:5]1[C:10]([Cl:11])=[CH:9][C:8]([Cl:12])=[C:7]([O:13][CH3:14])[CH:6]=1)=[O:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2735988N-(2,4-Dichloro-5-hydroxyphenyl)acetamide

Product 1

HCID 14593783N-(2,4-Dichloro-5-methoxyphenyl)acetamideYield 99.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 35.0 g (0.16 mole) of 2,4-dichloro-5-hydroxyacetanilide, 33.1 g (0.24 mole) of potassium carbonate, and 34.1 g (0.24 mole) of methyl iodide in 300 mL of acetone was heated at reflux for approximately 18 hours. The mixture was cooled and filtered. The filtrate was evaporated under reduced pressure to leave 37.4 g of 2,4-dichloro-5-methoxyacetanilide as a solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for approximately 18 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f2c8ea1609384ea7857ec011af102844
Source dataset
uspto-grants-1992_08
Patent number
US05136868

Reaction notes

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