Chloroacetyl chloride → 2-chloro-N-(3-methylphenyl)acetamide

HRID 490165Notes

Reaction equation

HRID 490165 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Cl:9][CH2:10][C:11](Cl)=[O:12]>[OH-].[Na+].ClCCl>[Cl: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 6577Chloroacetyl chlorideHCID 7934m-Toluidine

Product 1

HCID 2963252-chloro-N-(3-methylphenyl)acetamideYield 76.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

3-Methylaniline (1 g, 9.3 mmol) in 2N aqueous sodium hydroxide (30 mL) was treated with chloroacetyl chloride (0.82 mL, 10.27 mmol) dropwise at room temperature as a solution in dichloromethane. After 18 hours, the reaction mixture was quenched with water and the layers separated. The organic phase was washed with an aqueous solution of 1N HCl and dried over MgSO4, filtered and the filtrate concentrated under reduced pressure to provide 1.3 g (76%) of the title compound as a white solid. 1H NMR (300 MHz, CDCI3) δ 2.35 (s, 3H), 4.20 (s, 2H), 7.00 (s, 1H), 7.22 (m, 1H), 7.35-7.45 (m, 2H), 8.15 (br s, 1H); MS (DCI/NH3) m/e 201 (M+NH4)+.

Workup

  1. customthe reaction mixture was quenched with water
  2. customthe layers separated
  3. washThe organic phase was washed with an aqueous solution of 1N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-35094797d3e746bdbd4c5d75a88bc02b
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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