Acetyl chloride → HCID 59323098, compound

HRID 2390053Notes

Reaction equation

HRID 2390053 reaction equation
[CH2:1]([CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][N:6]1[C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH:2]([CH3:4])[CH3:3].[Cl-].[Al+3].[Cl-].[Cl-].[C:25](Cl)(=[O:27])[CH3:26]>C(=S)=S>[C:25]([C:10]1[CH:9]=[C:8]2[C:13]([CH2:14][CH:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[N:6]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH2:7]2)=[CH:12][CH:11]=1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 59323238HCID 59323238, compound

Product 1

HCID 59323098HCID 59323098, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Conditions

Temperature
45 °C

Procedure

A mixed liquid of 193 mg of 3-isobutyl-2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline, 533 mg of aluminum chloride, and 5 mL of carbon disulfide was added 157 mg of acetyl chloride at 44° C., followed by stirring at 45° C. for 1 hour. The reaction liquid was concentrated under reduced pressure, and 2N hydrochloric acid and ice were added thereto, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous sodium bicarbonate solution and then with brine, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation to obtain 202 mg (yield 91%) of a title compound as a yellow oily substance.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure, and 2N hydrochloric acid and ice
  3. additionwere added
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with an aqueous sodium bicarbonate solution
  6. dry with materialwith brine, and dried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-261213ac0e8141b9b91bfb7a4e9645be
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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