Sodium Chloride → HCID 178490529, compound

HRID 2225542Notes

Reaction equation

HRID 2225542 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][Cl:10].[CH3:11][C@@H:12]1[CH2:17][CH2:16][C@H:15]([NH:18][C:19](=[O:31])[CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([O:29][CH3:30])[CH:23]=2)[CH2:14][CH2:13]1.[Cl-].[Na+]>CC(CC(C)C)=O.C(Cl)Cl>[CH3:11][C@@H:12]1[CH2:13][CH2:14][C@H:15]([NH:18][C:19](=[O:31])[CH:20]=[CH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:8][CH2:9][Cl:10])=[C:24]([O:29][CH3:30])[CH:23]=2)[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 178490514HCID 178490514, compound

Product 1

HCID 178490529HCID 178490529, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

6.2 g of potassium carbonate and 4.2 ml of 1-bromo-2-chloroethane were added to a solution of 8.67 g of N-(cis-4-methylcyclohexyl)-4-hydroxy-3-methoxycinnamamide (Example 105) in 200 ml of methylisobutylketone. The solution was reacted for 10 hours, while it was refluxed. After reaction, the reaction solution was allowed to cool, added with 200 ml of methylene chloride and 200 ml of an aqueous sodium chloride solution, and subjected to extraction. The aqueous layer was extracted twice with 100 ml of methylene chloride. The organic layer obtained was washed twice with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The product obtained was recrystallized from methylene chloride/ether, yielding 8.76 g of N-(cis-4-methylcyclohexyl)-4-(2-chloroethoxy)-3-methoxycinnamamide (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 10 hours, while it
  2. temperaturewas refluxed
  3. customAfter reaction
  4. temperatureto cool
  5. extractionsubjected to extraction
  6. extractionThe aqueous layer was extracted twice with 100 ml of methylene chloride
  7. customThe organic layer obtained
  8. washwas washed twice with an aqueous sodium chloride solution
  9. dry with materialdried over magnesium sulfate
  10. customThereafter, the solvent was removed in vacuo
  11. customThe product obtained
  12. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-07edd511a53c4c3c84d23d778efc5420
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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