Sodium Iodide → HCID 178490532, compound

HRID 2225611Notes

Reaction equation

HRID 2225611 reaction equation
[I-:1].[Na+].[CH3:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:26])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22]Cl)=[C:16]([O:24][CH3:25])[CH:15]=2)[CH2:6][CH2:5]1>CC(CC)=O>[CH3:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([NH:10][C:11](=[O:26])[CH:12]=[CH:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][I:1])=[C:16]([O:24][CH3:25])[CH:15]=2)[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 178490530HCID 178490530, compound

Product 1

HCID 178490532HCID 178490532, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

19.5 g of sodium iodide was added to a solution of 4.57 g of N-(trans-4-methylcyclohexyl)-4-(2-chloroethoxy)-3-methoxycinnamamide (Example 138) in 300 ml of methylethylketone. The solution was stirred for 19 hours, while it was refluxed. After reaction, the reaction solution was washed three times with 200 ml of an aqueous sodium thiosulfate solution and once with an aqueous sodium chloride solution, and was dried over magnesium sulfate. Then, the solvent was removed in vacuo. The product obtained was recrystallized from methylene chloride/ether, yielding 4.86 g of N-(trans-4-methylcyclohexyl)-4-(2-iodoethoxy)-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. temperaturewas refluxed
  2. customAfter reaction
  3. washthe reaction solution was washed three times with 200 ml of an aqueous sodium thiosulfate solution
  4. dry with materialonce with an aqueous sodium chloride solution, and was dried over magnesium sulfate
  5. customThen, the solvent was removed in vacuo
  6. customThe product obtained
  7. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-af3556d0d0bb48b3a321e773789a03b0
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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