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

HRID 490158Notes

Reaction equation

HRID 490158 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Br:9][CH2:10][C:11](Cl)=[O:12]>[OH-].[Na+].ClCCl>[Br:9][CH2:10][C:11]([NH:5][C:4]1[CH:6]=[CH:7][CH:8]=[C:2]([CH3:1])[CH:3]=1)=[O:12]

Participants

5

Reactant 2

HCID 7934m-ToluidineHCID 89602Bromoacetyl chloride

Product 1

HCID 2255282-bromo-N-(3-methylphenyl)acetamideYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-Methylaniline (Acros, 15.50 mL, 141.8 mmol) in 2N aqueous sodium hydroxide (200 mL) at room temperature was treated with bromoacetyl chloride (Sigma, 12.50 mL, 152.0 mmol) as a solution in dichloromethane (200 mL). After 30 minutes, the layers were separated and the aqueous phase extracted with additional portions of dichloromethane. The organic phases were combined, washed with an aqueous solution of 1N HCl, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide 16.69 g (52% yield) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ2.28 (s, 3H), 4.01 (s, 2H), 6.91 (d, 1H, J=7.5 Hz), 7.20 (dd, 1H, J=7.5, 7.5 Hz), 7.36 (d, 1H, J=8.8 Hz), 7.42 (s, 1H), 10.28 (br s, 1H); MS (DCI/NH3) m/e 228/230 (M+H)+; 245/247 (M+NH4)+.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous phase extracted with additional portions of dichloromethane
  3. washwashed with an aqueous solution of 1N HCl
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-654db2a20bb140b3b6a6174ad8e76932
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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