Iodine → HCID 18794828, compound

HRID 400120Notes

Reaction equation

HRID 400120 reaction equation
[Mg].[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[N:11]([CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)[C:24]([O-:26])=[O:25])=[CH:18][CH:17]=1)[CH3:12].II.[CH3:37]O>>[O:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[N:11]([CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:22][CH:23]([O:27][C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)[C:24]([O:26][CH3:37])=[O:25])=[CH:20][CH:21]=1)[CH3:12]

Participants

5

Reactant 4

HCID 807IodineHCID 887MethanolHCID 5462224Magnesium2×HCID 18944088HCID 18944088, compound

Product 1

HCID 18794828HCID 18794828, compound

Procedure

Magnesium turnings (0.5 g) were added to a mixture of methyl (E/Z) 3-[4-[2-[N-(2-benzoxazolyl)-N-methylamino]ethoxy]phenyl]-2-(4-chlorophenoxy)propanoate (0.98 g) and a crystal of iodine dissolved in methanol (50 mL) at room temperature. The mixture was warmed gently with a heat gum until reaction ensued, at which pint the heating was stopped and the mixture stirred at room temperature during the addition, over ca 5 minutes, of a further portion of magnesium (2.00 g). The reaction mixture was immersed in a cold water bath and stirring continued until all the metal had dissolved (~4 hrs), then the mixture was evaporated in vacuo. The residue was suspended in water (100 mL) and stirred vigorously during the addition of concentrated hydrochloric acid, to give (once all the suspension had dissolved) a final pH of 1.5. The mixture was extracted with ethyl acetate (2×100 mL) and the combined ethyl acetate layers then washed with water (500 mL), brine (300 mL), dried (MgSO4) and evaporated. The resulting gum was chromatographed on silica gel with 3% ethyl acetate in dichloromethane as eluent to afford the title compound, mp 88°-90° C.

Workup

  1. temperatureThe mixture was warmed gently with a heat gum until reaction
  2. customThe reaction mixture was immersed in a cold water bath
  3. dissolutionhad dissolved (~4 hrs)
  4. customthe mixture was evaporated in vacuo
  5. stirringstirred vigorously during the addition of concentrated hydrochloric acid
  6. customto give (once all the suspension
  7. dissolutionhad dissolved) a final pH of 1.5
  8. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  9. washthe combined ethyl acetate layers then washed with water (500 mL), brine (300 mL)
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe resulting gum was chromatographed on silica gel with 3% ethyl acetate in dichloromethane as eluent

Sources & evidence

ORD record
ord-2a8d70f36a354f3da440894e5236867a
Source dataset
uspto-grants-1998_10
Patent number
US05827865

Reaction notes

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