Chloroacetyl chloride → HCID 19959496, compound

HRID 1661527Notes

Reaction equation

HRID 1661527 reaction equation
ClC[C:3](Cl)=[O:4].[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:17])[CH3:16])[CH:11]=[CH:12][CH:13]=1.[Cl-].[Al+3].[Cl-].[Cl-].C([O-])(=O)C.[Na+]>ClCCCl.O.C(OCC)(=O)C>[O:4]=[C:3]1[C:13]2[CH:12]=[CH:11][C:10]([NH:14][C:15](=[O:17])[CH3:16])=[CH:9][C:8]=2[O:7][CH2:6]1

Participants

8

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 11494Acetamide, N-(3-methoxyphenyl)-HCID 517045Sodium AcetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 19959496HCID 19959496, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

32.6 g (0.181 mol) of chloroacetyl chloride are added, followed within 15 minutes by 20 g (0.121 mol) of N-(3-methoxyphenyl)acetamide, to a solution of 64.6 g (0.484 mol) of aluminum chloride in 100 ml of 1,2-dichloroethane at 0° C. under argon. The temperature rises to 10° C. during this. The mixture is then slowly warmed to room temperature and stirred overnight. The brown mixture is added to ice-water, and ethyl acetate is added. After vigorous stirring, N-(3-methoxy-4-chloroacetylphenyl)acetamide precipitates and is filtered off with suction and dried under higher vacuum. The resulting solid is introduced into 140 ml of ethanol and, after addition of 13.2 g (0.154 mol) of sodium acetate, heated under reflux overnight. Cooling is followed by addition of water, and the ethanol is stripped off in a rotary evaporator. The precipitated solid is filtered off with suction on a frit and dried. 9.35 g (40% of theory) of the product result as a solid with a pale reddish color.

Workup

  1. customrises to 10° C.
  2. additionis added
  3. customAfter vigorous stirring, N-(3-methoxy-4-chloroacetylphenyl)acetamide precipitates
  4. filtrationis filtered off with suction
  5. customdried under higher vacuum
  6. additionThe resulting solid is introduced into 140 ml of ethanol
  7. temperatureheated
  8. temperatureunder reflux overnight
  9. temperatureCooling
  10. customthe ethanol is stripped off in a rotary evaporator
  11. filtrationThe precipitated solid is filtered off with suction on a frit
  12. customdried
  13. custom9.35 g (40% of theory) of the product result as a solid with a pale reddish color

Sources & evidence

ORD record
ord-567b274961584b9392d11fdb9019bbe1
Source dataset
uspto-grants-2011_10
Patent number
US08030347B2

Reaction notes

Loading…