Acetyl chloride → HCID 11196009, compound

HRID 2240190Notes

Reaction equation

HRID 2240190 reaction equation
[CH:1](O)(C)[CH3:2].C(=O)=O.[CH3:8][NH:9][C:10](=[O:24])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([Li])CCC.C(Cl)(=O)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:8][N:9]1[C:1]([CH3:2])=[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]1=[O:24]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 41285092-benzyl-N-methylbenzamideHCID 86586944Isopropanol carbon dioxideHCID 178418339Butyllithium

Product 1

HCID 11196009HCID 11196009, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

To an isopropanol/dry ice cooled solution of N-Methyl-2-(phenylmethyl) benzamide (1.00 g, 4.44 mmol) in THF (20 mL) under argon was added n-butyllithium solution (2.5M, 4.44 mL, 11.1 mmol) dropwise. After 10 min. neat acetyl chloride (0.447 mL, 6.66 mmol) was slowly added to the reaction solution. The contents of the reaction flask were allowed to warm to room temperature and after 2 h the reaction was quenched with saturated ammonium chloride. The mixture was extracted with ether (3×) and then the combined organic portions were washed with brine and dried with anhydrous sodium sulfate. Filtration followed by evaporation of solvent in vacuo gave the crude product which was subjected to flash column chromatography (hexane:ethyl acetate 70:30 then 50:50) to afford the title compound as a white solid.

Workup

  1. customwas quenched with saturated ammonium chloride
  2. extractionThe mixture was extracted with ether (3×)
  3. washthe combined organic portions were washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation of solvent in vacuo
  7. customgave the crude product which

Sources & evidence

ORD record
ord-3088dd9b968648beb78bbe0807a2f801
Source dataset
uspto-grants-2010_05
Patent number
US07723352B2

Reaction notes

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