Hydrochloric Acid → HCID 178466529, compound

HRID 2225602Notes

Reaction equation

HRID 2225602 reaction equation
[CH3:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:24])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20]Cl)=[C:14]([O:22][CH3:23])[CH:13]=2)[CH2:4][CH2:3]1.[H-].[Na+].Cl>C1COCC1>[CH3:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([NH:8][C:9](=[O:24])[CH:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH:19]=[CH2:20])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 178490530HCID 178490530, compound

Product 1

HCID 178466529HCID 178466529, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.9 g of N-(trans-4-methylcyclohexyl)-4-(2-chloroethoxy )- 3-methoxycinnamamide (Example 138 ) was added to a solution of 0.5 g of sodium hydride in 50 ml of THF. The solution was reacted for 72 hours, while it was refluxed. After reaction, 2 N hydrochloric acid was added to the reaction solution, acidifying the solution, and the solution was extracted with 100 ml of methylene chloride. The organic layer obtained was dried over magnesium sulfate, and the solvent was removed in vacuo. The product obtained was recrystallized from methylene chloride/ether, yielding 0.54 g of N-(trans-4-methylcyclohexyl)-4-vinyloxy-3-methoxycinnamamide (a compound of the present invention ) as white crystal, which had the following physiochemical properties:

Workup

  1. customThe solution was reacted for 72 hours, while it
  2. temperaturewas refluxed
  3. additionwas added to the reaction solution
  4. extractionthe solution was extracted with 100 ml of methylene chloride
  5. customThe organic layer obtained
  6. dry with materialwas dried over magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customThe product obtained
  9. customwas recrystallized from methylene chloride/ether

Sources & evidence

ORD record
ord-abd27cdb36bb447aa5a8816657a12e0b
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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