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

HRID 1465669Notes

Reaction equation

HRID 1465669 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 mixed with aluminum chloride (9.1 g, 68 mmol). The reaction mixture was heated at reflux for 30 min, cooled to room temperature, and allowed to 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 with 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-d8cb35b0256c435aa2b8c82dfd446949
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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