Chloroacetyl chloride → 2-chloro-N-(3,5-dimethylphenyl)acetamide

HRID 490162Notes

Reaction equation

HRID 490162 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[Cl:10][CH2:11][C:12](Cl)=[O:13]>[OH-].[Na+].ClCCl>[Cl:10][CH2:11][C:12]([NH:5][C:4]1[CH:6]=[C:7]([CH3:9])[CH:8]=[C:2]([CH3:1])[CH:3]=1)=[O:13]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 79493,5-Dimethylaniline

Product 1

HCID 15228732-chloro-N-(3,5-dimethylphenyl)acetamideYield 94.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

3,5-Dimethylaniline (Acros, 10.50 mL, 84.05 mmol) in 2N sodium hydroxide (200 mL) was treated with chloroacetyl chloride (Acros, 10.00 mL, 125.7 mmol) as a solution in dichloromethane (200 mL) drop wise. After 18 hours, the layers were separated. The organic phase was washed with 1N hydrochloric acid, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure to provide 15.64 g (94%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.24 (s, 6H), 4.21 (s, 2H), 6.73 (s, 1H), 7.20 (s, 2H), 10.11 (br s, 1H); MS (DCI/NH3) m/e 198 (M+H)+.

Workup

  1. customthe layers were separated
  2. washThe organic phase was washed with 1N hydrochloric acid
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-225bfdf6b3b7427dbf7feea6fd7d478b
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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