Acetyl chloride → HCID 12049814, compound

HRID 430007Notes

Reaction equation

HRID 430007 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:7])[CH3:6].[C:9]1([S:15]([O:18][C:19]2[CH:27]=[CH:26][C:22]3[S:23][CH:24]=[CH:25][C:21]=3[CH:20]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[C:5]([C:25]1[C:21]2[CH:20]=[C:19]([O:18][S:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)(=[O:16])=[O:17])[CH:27]=[CH:26][C:22]=2[S:23][CH:24]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 12049813HCID 12049813, compound

Product 1

HCID 12049814HCID 12049814, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Powdered aluminum chloride (1.34 g, 10 mmol) was suspended in dichloromethane (10 ml). To the suspension was added dropwise acetyl chloride (1.02 ml, 14.3 mmol) over 5 minutes with stirring and under ice-cooling. Subsequently, a solution of the compound (8) (2.075 g, 7.2 mmol) prepared above in dichloromethane (6 ml) was added dropwise over 15 minutes. After being stirred for 2 hours at the same temperature and then for 2.5 hours at room temperature, the solution was poured into ice-water and extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate and then the solvent was distilled off under reduced pressure. The resulting residue was recrystallized from ethyl acetate (3 ml) and hexane (3 ml) to provide 2.01 g of the title compound (9). Yield: 84.4% mp 129-130° C.

Workup

  1. temperaturecooling
  2. additionwas added dropwise over 15 minutes
  3. stirringAfter being stirred for 2 hours at the same temperature
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was recrystallized from ethyl acetate (3 ml) and hexane (3 ml)

Sources & evidence

ORD record
ord-77535500711c4f3db756b11fc3791384
Source dataset
uspto-grants-2001_11
Patent number
US06320060B1

Reaction notes

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