Potassium Iodide → HCID 11195696, compound

HRID 1671712Notes

Reaction equation

HRID 1671712 reaction equation
Cl[CH2:2]/[CH:3]=[CH:4]\[CH2:5]Cl.[NH2:7][CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])(=O)C.[Na+].[I-].[K+]>CO>[C:15]1([CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:7]2[CH2:5][CH:4]=[CH:3][CH2:2]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7036BenzhydrylamineHCID 517045Sodium AcetateHCID 64321151,4-Dichloro-cis-2-butene

Product 1

HCID 11195696HCID 11195696, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

cis-1,4-Dichloro-2-butene (15.4 g) was dissolved in methanol (100.0 mL). Aminodiphenylmethane (18.3 g), sodium acetate (16.4 g), and potassium iodide (1.0 g) were added to the solution, and the mixture was stirred at 65° C. for 6.5 hours. The reaction mixture was extracted with methylene chloride and 1 mol/L aqueous sodium hydroxide, and the organic layer was dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure. Isopropyl ether was added to the residue, and the mixture was heated. The insoluble material was removed through filtration, and the filtrate was concentrated. The formed crystals were collected through filtration. The crystals were further washed with a small amount of isopropyl ether, to thereby give the target compound (11.62 g, yield 41%) as white crystals.

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride and 1 mol/L aqueous sodium hydroxide
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customThe drying agent was removed through filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionIsopropyl ether was added to the residue
  6. temperaturethe mixture was heated
  7. customThe insoluble material was removed through filtration
  8. concentrationthe filtrate was concentrated
  9. filtrationThe formed crystals were collected through filtration
  10. washThe crystals were further washed with a small amount of isopropyl ether

Sources & evidence

ORD record
ord-9fe2f22321b241bc90f06624e67bee28
Source dataset
uspto-grants-2011_08
Patent number
US07994344B2

Reaction notes

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