Chloroacetyl chloride → 2-chloro-N-(2,4-dimethoxyphenyl)acetamide

HRID 2266154Notes

Reaction equation

HRID 2266154 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:4]=1[NH2:5].C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:19][CH2:20][C:21]([NH:5][C:4]1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[CH:9][C:3]=1[O:2][CH3:1])=[O:22]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 176522,4-Dimethoxyaniline

Product 1

HCID 3038242-chloro-N-(2,4-dimethoxyphenyl)acetamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2,4-dimethoxy aniline (30.6 g, 0.2 mol), triethylamine (27.9 mL, 0.2 mol) in 600 mL methylene choride was stirred at 0° C. under nitrogen. Chloroacetyl chloride (16 mL, 0.2 mol) was added dropwise, and the reaction mixture was stirred for 15 minutes at 0° C., and then stirred for an additional two hours during which time the reaction mixture was allowed to warm to room temperature. The reaction was quenched by addition of 1N HCl, followed by saturated aqueous sodium bicarbonate. The aqueous mixture was partitioned with EtOAc, and the organic phase was separated, dried (MgSO4), filtered, and evaporated under reduced pressure to give 45.58 g of crude 2-Chloro-N-(2,4-dimethoxy-phenyl)-acetamide. MS (M+H)=230.

Workup

  1. stirringthe reaction mixture was stirred for 15 minutes at 0° C.
  2. stirringstirred for an additional two hours during which time the reaction mixture
  3. temperatureto warm to room temperature
  4. customThe reaction was quenched by addition of 1N HCl
  5. customThe aqueous mixture was partitioned with EtOAc
  6. customthe organic phase was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0a105815eb1343049a5f56d937dc4a0b
Source dataset
uspto-grants-2010_12
Patent number
US07858632B2

Reaction notes

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