Hydrochloric Acid → 2-chloro-N-(5-methoxy-2-methylphenyl)acetamide

HRID 1066261

Reaction equation

HRID 1066261 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([CH:9]=1)[NH2:8].C(N(CC)CC)C.[Cl:18][CH2:19][C:20](Cl)=[O:21].Cl>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH3:10])=[C:7]([NH:8][C:20](=[O:21])[CH2:19][Cl:18])[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 995005-Methoxy-o-toluidine

Product 1

HCID 11328892-chloro-N-(5-methoxy-2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-2-methylaniline (7.62 g) and triethylamine (15.5 ml) in dichloromethane (150 ml) at 0-5° C. was added chloroacetyl chloride (5.0 ml) dropwise and the ice bath removed. The resulting reaction mixture was stirred for 45 min before being poured into dil HCl and extracted with dichloromethane. Organic extracts were combined, washed with water, dried (Na2SO4) and concentrated to give a brown solid that was triturated with diethyl ether to leave the sub-title compound as a beige solid (5.7 g).

Workup

  1. customthe ice bath removed
  2. customThe resulting reaction mixture
  3. extractionextracted with dichloromethane
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give a brown solid that
  8. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-dfa0a48bffc6424384cdfa0f59d777dd
Source dataset
uspto-grants-2001_06
Patent number
US06242470B1

Linked notes

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