m-Toluidine → 2-bromo-N-(3-methylphenyl)acetamide

HRID 2377268Notes

Reaction equation

HRID 2377268 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=1.[OH-].[Na+].[Br:11][CH2:12][C:13](Cl)=[O:14]>ClCCl>[Br:11][CH2:12][C:13]([NH:1][C:2]1[CH:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1)=[O:14]

Participants

5

Reactant 3

HCID 7934m-ToluidineHCID 14798Sodium HydroxideHCID 89602Bromoacetyl chloride

Product 1

HCID 2255282-bromo-N-(3-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a slurry of m-toluidine (15.5 mL, 140 mmol) in a 2N aqueous solution of sodium hydroxide (75 mL) was added dropwise a solution of bromoacetyl chloride (11.6 mL, 140 mmol) in dichloromethane (50 mL) and the reaction mixture was stirred at room temperature for about 30 min. The layers were separated and the organic layer was washed with 1N aqueous hydrochloric acid, dried (MgSO4), filtered and concentrated under vacuum. The residue was triturated twice from dichloromethane/hexane (1:4) to provide 2-bromo-N-m-tolyl-acetamide. MS (DCI-NH3): m/z 245, 247 (M+NH3)+.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with 1N aqueous hydrochloric acid
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was triturated twice from dichloromethane/hexane (1:4)

Sources & evidence

ORD record
ord-d48ea276fc0c4cb981733fa548f4f2ad
Source dataset
uspto-grants-2008_12
Patent number
US07468371B2

Reaction notes

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