Hydrochloric Acid → 2-Chloro-N-(2,6-dimethylphenyl)acetamide

HRID 1460640Notes

Reaction equation

HRID 1460640 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:8]=1[NH2:9].C(N(CC)CC)C.Cl>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:9][C:8]1[C:10]([CH3:14])=[CH:11][CH:12]=[CH:13][C:7]=1[CH3:6])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 68962,6-DimethylanilineHCID 8471Triethylamine

Product 1

HCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloroacetyl chloride (4.0 g) in methylene chloride (25 ml) was cooled via an ice bath to 0° C. A solution of 2,6-dimethylaniline (4.25 g) and triethylamine (5 ml) in methylene chloride (25 ml) was added dropwise over 1 hour and the resulting solution stirred and allowed to come to room temperature for a 20 hour period. 10% Hydrochloric acid was added and the layers were separated. The organic layer was washed with 1N hydrochloric acid and water, dried over sodium sulfate, filtered and the solvent removed to give a solid which was recrystallized from benzene. The structure was confirmed by NMR.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with 1N hydrochloric acid and water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent removed
  6. customto give a solid which
  7. customwas recrystallized from benzene

Sources & evidence

ORD record
ord-715603c28d7945dfa97bb37930d857ca
Source dataset
uspto-grants-1991_12
Patent number
US05071876

Reaction notes

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