Acetyl chloride → N-(4-acetyl-3-chloro-5-methylphenyl)acetamide

HRID 1843805Notes

Reaction equation

HRID 1843805 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:13](Cl)(=[O:15])[CH3:14].[Cl-].[Al+3].[Cl-].[Cl-]>C(=S)=S>[C:13]([C:7]1[C:6]([CH3:8])=[CH:5][C:4]([NH:9][C:10](=[O:12])[CH3:11])=[CH:3][C:2]=1[Cl:1])(=[O:15])[CH3:14]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 587955Acetamide, N-(3-chloro-5-methylphenyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 58442558N-(4-acetyl-3-chloro-5-methylphenyl)acetamideYield 85.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A dry CS2 solution (30 mL) containing N-(3-chloro-5-methyl-phenyl)acetamide (5.0 g, 27 mmol) and acetyl chloride (2.9 ml, 40.8 mmol) was slowly added with aluminum chloride (9.1 g, 68 mmol). The reaction mixture was heated at reflux for 30 min, cooled to room temperature, and stand for 4.0 h. The CS2 was decanted and the remaining syrup was poured into icy HCl. The resultant solids were collected, re-dissolved in EtOH, and decolorized by charcoal. The solution was filtered and the filtrate was concentrated under vacuum to give N-(4-acetyl-3-chloro-5-methylphenyl)acetamide (5.2 g) as light yellow solids in 85% yield: 1H NMR (500 MHz, CDCl3) δ 7.48 (s, 1 H), 7.26 (s, 1 H), 7.21 (s, 1 H), 2.52 (s, 3 H), 2.24 (s, 3 H), 2.18 (s, 3 H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 30 min
  3. customThe CS2 was decanted
  4. additionthe remaining syrup was poured into icy HCl
  5. customThe resultant solids were collected
  6. dissolutionre-dissolved in EtOH
  7. filtrationThe solution was filtered
  8. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3213c6040a1e47cab99ea5f24fbbfb6a
Source dataset
uspto-grants-2015_02
Patent number
US08946268B2

Reaction notes

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