Potassium Iodide → HCID 22715141, compound

HRID 352117Notes

Reaction equation

HRID 352117 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH2:13]Cl.[CH3:21][NH:22][CH2:23][CH2:24][OH:25].[I-].[K+].[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>CN1CCCC1.O>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH2:13][N:22]([CH3:21])[CH2:23][CH2:24][OH:25]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 80162-(Methylamino)ethanolHCID 444972Fumaric AcidHCID 22715106HCID 22715106, compound

Product 1

HCID 22715141HCID 22715141, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 84541-MethylpyrrolidineSolvent

Procedure

A solution of the product from step (b) (0.20 g, 0.61 mmol), 2-(methylamino)ethanol (0.137 g,) 1.83 mmol) and potassium iodide (0.051 g, 0.31 mmol) in N-methylpyrrolidine was heated to 100° C. in a sealed vessel and stirred for 4 h. The reaction was cooled and poured into water (50 ml) and the mixture extracted with ethyl acetate (3×50 ml). The combined organic extracts were washed with water (3×30 ml), dried (magnesium sulphate) and evaporated. The residue was dissolved in methanol and treated with one equivalent of fumaric acid, stirred for ten minutes, then the solvent was removed in vacuo. The solid residue was triturated with ethyl acetate and the white solid obtained filtered off and dried to give the title compound (0.155 g).

Workup

  1. temperatureThe reaction was cooled
  2. extractionthe mixture extracted with ethyl acetate (3×50 ml)
  3. washThe combined organic extracts were washed with water (3×30 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated
  6. dissolutionThe residue was dissolved in methanol
  7. stirringstirred for ten minutes
  8. customthe solvent was removed in vacuo
  9. customThe solid residue was triturated with ethyl acetate
  10. customthe white solid obtained
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-f6eb900e2fe54b24ac32cda31ea911f0
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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