Acetyl chloride → HCID 10352530, compound

HRID 2268171Notes

Reaction equation

HRID 2268171 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl-].[Cl-].[Cl-].[Al+3].C[O:10][C:11]1[CH:19]=[C:18]2[C:14]([CH2:15][C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1>C(=S)=S>[C:1]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:11]=1[OH:10])[NH:17][C:16](=[O:20])[CH2:15]2)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 27937496-MethoxyoxindoleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10352530HCID 10352530, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

Acetyl chloride (4.09 mL, 0.0575 mol) was added to a slurry of aluminum trichloride (AlCl3) (35.36 g, 0.265 mol) in carbon disulfide (CS2) (250 mL). After 2-3 min, 6-methoxyoxindole (7.22 g, 0.0442 mol) was added. The resulting mixture was heated to reflux for 2.5 hours. (A black tar developed with time). Excess solvent was decanted and ice water was added carefully to the residue. The resulting mixture was stirred overnight. The pale yellow solid obtained was collected, washed with water and dried under high vacuum to give the title compound (7.32 g, 87%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 2.5 hours
  3. customExcess solvent was decanted
  4. additionice water was added carefully to the residue
  5. customThe pale yellow solid obtained
  6. customwas collected
  7. washwashed with water
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-dc76ba13d4ff461aaaad0f047811551e
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

Loading…