2-Methoxyaniline → 4-Chloromethyl-N-(2-methoxyphenyl)benzamide

HRID 2418

Reaction equation

HRID 2418 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[Cl:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1>C(Cl)Cl>[Cl:12][CH2:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 70002-MethoxyanilineHCID 14798Sodium HydroxideHCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamideYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

o-Anisidine (0.69 ml, 6.0 mmol) was dissolved in methylene chloride (10 ml) and, with cooling in an ice bath, mixed with 20% sodium hydroxide (5 ml) and 4-chloromethylbenzoyl chloride (1.17 g, 6.0 mmol). After 30 minutes of stirring at the same temperature, the reaction mixture was extracted with methylene chloride and then washed with 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate, the solvent was removed by evaporation, and the resulting light beige solid was purified by recrystallization (ether-hexane) to obtain 1.56 g (94.2%) of the title compound in the form of colorless needle crystals.

Workup

  1. temperaturewith cooling in an ice bath
  2. extractionthe reaction mixture was extracted with methylene chloride
  3. washwashed with 1N hydrochloric acid, water and saturated brine in that order
  4. dry with materialAfter drying on anhydrous magnesium sulfate
  5. customthe solvent was removed by evaporation
  6. customthe resulting light beige solid was purified by recrystallization (ether-hexane)

Sources & evidence

ORD record
ord-77cb8f49e98843759fa1c7777b2640d4
Source dataset
uspto-grants-1998_03
Patent number
US05728835

Linked notes

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