Potassium Iodide → HCID 13745824, compound

HRID 1826231Notes

Reaction equation

HRID 1826231 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.[P:12]([O:19]CC)([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15].[I-].[K+].C(#N)C>O>[C:7]([C:6]1[CH:10]=[CH:11][C:3]([CH2:2][P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])=[CH:4][CH:5]=1)(=[O:8])[NH2:9]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 31215Triethyl phosphiteHCID 4583634-(Chloromethyl)benzamide

Product 1

HCID 13745824HCID 13745824, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The compound (44.83 g, 0.264 mol) obtained in Example 1, triethyl phosphite (53.21 g, 0.320 mol), potassium iodide (39.4 g, 0.237 mol) and acetonitrile (224 mL) were charged and stirred under reflux for 4 hrs. The reaction mixture was allowed to return to room temperature, and water (336 mL) was added. The mixture was concentrated under reduced pressure, and the residue (315 g) was stirred at room temperature for 1 hr. and under ice-cooling for 1 hr. The crystals were collected by filtration, washed with cold water (20 mL) and dried in vacuo at 40° C. for 7 hrs. to give the title compound (66.79 g, yield 93.2%) as slightly yellow crystals.

Workup

  1. temperatureunder reflux for 4 hrs
  2. customto return to room temperature
  3. concentrationThe mixture was concentrated under reduced pressure
  4. stirringthe residue (315 g) was stirred at room temperature for 1 hr
  5. temperatureand under ice-cooling for 1 hr
  6. filtrationThe crystals were collected by filtration
  7. washwashed with cold water (20 mL)
  8. customdried in vacuo at 40° C. for 7 hrs

Sources & evidence

ORD record
ord-00444d0b57af44368b400557052bdcc7
Source dataset
uspto-grants-2006_05
Patent number
US07049441B2

Reaction notes

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