Acetyl chloride → HCID 86584269, compound

HRID 382491Notes

Reaction equation

HRID 382491 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH3:9][N:10]([CH3:31])[C:11](=[O:30])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH:19][C:20]1[C:25]([F:26])=[C:24]([F:27])[CH:23]=[C:22]([F:28])[C:21]=1[F:29]>ClCCCl>[CH3:31][N:10]([CH3:9])[C:11](=[O:30])[CH2:12][C:13]1[CH:18]=[C:17]([C:1](=[O:3])[CH3:2])[CH:16]=[CH:15][C:14]=1[NH:19][C:20]1[C:21]([F:29])=[C:22]([F:28])[CH:23]=[C:24]([F:27])[C:25]=1[F:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 86593055HCID 86593055, compound

Product 1

HCID 86584269HCID 86584269, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Under an inert atmosphere, acetyl chloride (29.1 ml, 0.385 mol) is slowly added to a suspension of aluminum chloride (51.2 g, 0.385 mol) stirred in 1,2-dichloroethane (750 ml). After stirring at room temperature for 1 hour a yellow solution is obtained. The solution is cooled in an ice bath and N,N-dimethyl-2-(2′,3′,5′,6′-tetrafluoroanilino)phenylacetamide (40 g, 0.123 mol) is added. The reaction is allowed to warm to room temperature and then warmed to 80° for 0.5 hours. The reaction is poured over ice and extracted with EtOAc (2×750 ml). The organic extract is washed with water (750 ml), saturated NaHCO3 solution (500 ml) and brine (500 ml). Evaporation on a rotovap and trituration with Et2O gives N,N-dimethyl-5-acetyl-2-(2′,3′,5′,6′-tetrafluoroanilino)phenylacetamide as a white solid, m.p. 112-114°.

Workup

  1. customis obtained
  2. temperatureThe solution is cooled in an ice bath
  3. temperatureto warm to room temperature
  4. temperaturewarmed to 80° for 0.5 hours
  5. additionThe reaction is poured over ice
  6. extractionextracted with EtOAc (2×750 ml)
  7. extractionThe organic extract
  8. washis washed with water (750 ml), saturated NaHCO3 solution (500 ml) and brine (500 ml)
  9. customEvaporation on a rotovap and trituration with Et2O

Sources & evidence

ORD record
ord-f3a29fc9dbb74d9e9346fda466dc306d
Source dataset
uspto-grants-2001_10
Patent number
US06310099B1

Reaction notes

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