Potassium Iodide → HCID 12417380, compound

HRID 1658819Notes

Reaction equation

HRID 1658819 reaction equation
[NH:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Cl>CS(C)=O.O>[F:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][N:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 84532-ImidazolidinoneHCID 99743-Fluorobenzyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 12417380HCID 12417380, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A 21.5 g (0.25 mole) portion of 2-imidazolidinone in 150 ml of dimethylsulfoxide was treated with 34.5 g (0.25 mole) of potassium carbonate, 20 g (0.12 mole) of potassium iodide and 36.3 g (0.25 mole) of 3-fluorobenzyl chloride. The reaction mixture was heated with rapid stirring to 100° over 0.3 hours, held at 100° for 1.8 hours and poured with rapid stirring into 1.5 l of cold water. The aqueous mixture was extracted with 1.3 l of chloroform. The chloroform extract was washed with 500 ml of water, dried over magnesium sulfate overnight and filtered. The filtrate was concentrated to dryness to give 46 g (94%) of a light green semi-solid. The crude product was washed with 125 ml of ether, filtered and air dried to give 13.5 g (28%) of a white solid, m.p. 103°-105°.

Workup

  1. temperatureThe reaction mixture was heated
  2. waitheld at 100° for 1.8 hours
  3. additionpoured
  4. extractionThe aqueous mixture was extracted with 1.3 l of chloroform
  5. extractionThe chloroform extract
  6. washwas washed with 500 ml of water
  7. dry with materialdried over magnesium sulfate overnight
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-5887b4776cee4cc6a967e3a81f36a376
Source dataset
uspto-grants-1976_06
Patent number
US03966758

Reaction notes

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