Water → HCID 816842, compound

HRID 911712Notes

Reaction equation

HRID 911712 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].[Cl-].[Cl-].[Cl-].[Al+3].O>C1(C)C=CC=CC=1.C(OCC)C>[CH3:1][C:3]1[CH:11]=[CH:10][C:6]([C:7]([C:6]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 962WaterHCID 801724-Cyanobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 816842HCID 816842, compoundYield 97.9%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

Suspend 4-cyanobenzoyl chloride (2.0 g, 12 mmol) in anhydrous toluene (30 mL). Add aluminum trichloride (2.4 g, 18 mmol) in three portions and stir the reaction mixture at ambient temperature overnight. Cool to 0° C., add carefully water and extract the mixture twice with EtOAc. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to give a solid. Suspend the solid in diethyl ether and filter to obtain the desired intermediate (1.30 g, 49%) that was used without any further purification. GC-MS m/z: 221 (Me).

Workup

  1. extractionextract the mixture twice with EtOAc
  2. dry with materialDry the combined organic extracts over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto give a solid
  6. filtrationfilter

Sources & evidence

ORD record
ord-aa71689b27824ebcbec2471aa4b7a42f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…