Sodium Hydroxide → HCID 178449230, compound

HRID 463784Notes

Reaction equation

HRID 463784 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH2:8]([NH:12][C:13]([NH2:15])=[NH:14])[CH:9]([CH3:11])[CH3:10].S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:23][C:24]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:25]=1[CH:26]=[CH:27][C:28](Cl)=[O:29]>O1CCCC1>[ClH:23].[Cl:23][C:24]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:25]=1[CH:26]=[CH:27][C:28]([NH:14][C:13]([NH:12][CH2:8][CH:9]([CH3:11])[CH3:10])=[NH:15])=[O:29]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 403983-(2,6-Dichlorophenyl)prop-2-enoyl chlorideHCID 178449235Isobutylguanidine sulfate

Product 1

HCID 178449230HCID 178449230, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 7.62 g of a 50% aqueous sodium hydroxide solution, 15.65 g isobutylguanidine sulfate and 120 ml of tetrahydrofuran is stirred for 45 minutes. 12 g of anhydrous sodium sulfate are added to the mixture and stirring continued for 40 minutes. A solution of 2,6-dichlorocinnamoyl chloride (11.22 g) in 40 ml of anhydrous tetrahydrofuran is added dropwise, and the reaction mixture stirred overnight. The yellow reaction mixture is filtered, concentrated in vacuo and the resulting yellow oil partitioned between 100 ml of methylene chloride and 150 ml of H2O. The aqueous layer is extracted with methylene chloride, the combined organic extract dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to a yellow oil. The resulting oil is dissolved in hot acetonitrile/methanol, filtered and evaporated on a hot plate. A white solid is collected, M.P. 178°-180° C.

Workup

  1. stirringstirring
  2. waitcontinued for 40 minutes
  3. stirringthe reaction mixture stirred overnight
  4. filtrationThe yellow reaction mixture is filtered
  5. concentrationconcentrated in vacuo
  6. customthe resulting yellow oil partitioned between 100 ml of methylene chloride and 150 ml of H2O
  7. extractionThe aqueous layer is extracted with methylene chloride
  8. extractionthe combined organic extract
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo to a yellow oil
  12. dissolutionThe resulting oil is dissolved in hot acetonitrile/methanol
  13. filtrationfiltered
  14. customevaporated on a hot plate
  15. customA white solid is collected

Sources & evidence

ORD record
ord-5a9ac91674c6448ab6ba484d73983a35
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

Loading…