Acetyl chloride → HCID 19600991, compound

HRID 610078Notes

Reaction equation

HRID 610078 reaction equation
[F:1][C:2]([F:15])([F:14])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][C:5]1=[O:13].[C:16](Cl)(=[O:18])[CH3:17].[Cl-].[Cl-].[Cl-].[Al+3]>C(=S)=S>[C:16]([C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[N:4]([CH2:3][C:2]([F:1])([F:14])[F:15])[C:5](=[O:13])[CH2:6]2)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 196009761,3-Dihydro-1-(2,2,2-trifluoroethyl)-2H-indol-2-one

Product 1

HCID 19600991HCID 19600991, compound

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of 1-(2,2,2-trifluoro-ethyl)-1,3-dihydro-indol-2-one (2.0 g, 9.3 mmol) and acetyl chloride (0.86 mL, 12 mmol) in carbon disulfide (40 mL) was added aluminum trichloride (7.4 g, 56 mmol) by portions. The mixture was heated to reflux for 3 hours, then cooled. The liquid phase was decanted and the residue was quenched carefully with ice, then water. The solids were filtered, washed with water, dried and recrystallized from acetone/hexanes to give a pale pink solid, mp 170-171° C. Yield 1.23 g (51%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. customThe liquid phase was decanted
  5. customthe residue was quenched carefully with ice
  6. filtrationThe solids were filtered
  7. washwashed with water
  8. customdried
  9. customrecrystallized from acetone/hexanes
  10. customto give a pale pink solid, mp 170-171° C

Sources & evidence

ORD record
ord-5c6b02960a8a422ca3d010efc9cecdb6
Source dataset
uspto-grants-1999_12
Patent number
US05998463

Reaction notes

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