Potassium Iodide → HCID 12805910, compound

HRID 1659594Notes

Reaction equation

HRID 1659594 reaction equation
[CH2:1]1[O:10][C:4]([CH2:6][CH2:7][CH2:8]Cl)([CH3:5])[O:3][CH2:2]1.[CH3:11][NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[CH2:1]1[O:10][C:4]([CH2:6][CH2:7][CH2:8][N:12]([CH3:11])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([CH3:5])[O:3][CH2:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7515N-MethylanilineHCID 11430Potassium CarbonateHCID 800792-(3-Chloropropyl)-2-methyl-1,3-dioxolane

Product 1

HCID 12805910HCID 12805910, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 5-chloro-2-pentanone ethylene ketal (80 g=0.49 mol), N-methylaniline (52 g=0.49 mol), potassium carbonate (67 g=0.49 mol) and potassium iodide (8.1 g) in 250 ml dimethylformamide and heat at 100° C. for 16 hours. Allow to cool, partition between ether and water, and wash the ether twice with water. Dry, concentrate and distill to obtain 5-(N-methylanilino)-2-pentanone ethylene ketal, boiling point 104°-109° C./0.1 mm. Dissolve this (47 g=0.20 mol) in 400 ml 1.0 N hydrochloric acid with 100 ml ethanol. Let stand 2 hours, concentrate and adjust pH to about 8. Extract with ethyl ether, dry, concentrate and distill to obtain the product, having a boiling point 100°-104° C./0.1 mm pressure.

Workup

  1. temperatureAllow to cool
  2. custompartition between ether and water
  3. washwash the ether twice with water
  4. customDry
  5. concentrationconcentrate
  6. distillationdistill

Sources & evidence

ORD record
ord-c59ce869076b4c6aa7221134d6215c79
Source dataset
uspto-grants-1981_12
Patent number
US04304790

Reaction notes

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