Potassium Carbonate → HCID 43333337, compound

HRID 2244018Notes

Reaction equation

HRID 2244018 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1>CC(C)=O>[Cl:16][CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[O:23])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133964-AminobenzonitrileHCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 43333337HCID 43333337, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add 4-aminobenzonitrile (3.125 g, 26.4 mmol) and potassium carbonate (8.04 g, 58.2 mmol) to a solution of 4-chloromethyl-benzoyl chloride (5.00 g, 26.4 mmol) in acetone (60 mL). Heat at reflux for 4 hours. Cool to room temperature, filter, and concentrate to afford the title compound as a yellow solid (7.30 g, 91%): 1H NMR (DMSO-d6) δ 4.86 (s, 2H), 7.61 (d, 2H), 7.83 (d, 2H), 7.94-8.03 (m, 4H), 10.72 (s, 1H).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 4 hours
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-f649a610c95a42a79a173a6ef64bb0ed
Source dataset
uspto-grants-2010_03
Patent number
US07678794B2

Reaction notes

Loading…