Aniline → Chloroacetanilide

HRID 560115Notes

Reaction equation

HRID 560115 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:15][CH2:16][C:17](Cl)=[O:18].OS([O-])(=O)=O.[K+]>C(Cl)Cl>[Cl:15][CH2:16][C:17]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:18]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 516920Potassium bisulfate

Product 1

HCID 11485Chloroacetanilide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

At 0° C. to a solution of aniline (2.45 mL) and triethylamine (0.73 mL) in methylene chloride (30 mL) a solution of chloroacetyl chloride (2.56 mL) in methylene chloride (10 mL) was added dropwise. The reaction was stirred at 0° C. for 30 min and then at room temperature for 1 hour. A 1M aqueous solution of KHSO4 was added, the phases were separated and the inorganic one was extracted with ethyl acetate (×3). The combined organic layers were washed with water, brine, dried (Na2SO4) and concentrated in vacuo to yield crude 2-chloro-N-phenyl-acetamide, which was subjected to the next reaction without further purification.

Workup

  1. waitat room temperature for 1 hour
  2. customthe phases were separated
  3. extractionthe inorganic one was extracted with ethyl acetate (×3)
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d56c82fd3364dce9a7491c4f06e692a
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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