Sodium Hydroxide → HCID 178449229, compound

HRID 463781Notes

Reaction equation

HRID 463781 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+].[C:23]([Cl:33])(=[O:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[ClH:33].[C:23]([NH:14][C:13]([NH:12][CH2:8][CH:9]([CH3:11])[CH3:10])=[NH:15])(=[O:32])[CH:24]=[CH:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 660233-Phenylprop-2-enoyl chlorideHCID 178449235Isobutylguanidine sulfate

Product 1

HCID 178449229HCID 178449229, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 7.95 g of a 50% aqueous sodium hydroxide solution, isobutylguanidine sulfate (16.32 g), and 120 ml of tetrahydrofuran is stirred for 45 minutes. 12 g anhydrous sodium sulfate are added to the mixture and stirring continued 45 minutes. A solution of cinnamoyl chloride (8.28 g) in anhydrous tetrahydrofuran is slowly added dropwise to the reaction mixture and stirring continued for 48 hrs. The reaction mixture is filtered and concentrated in vacuo. The resultant yellow solid is partitioned between 150 ml of water and 125 ml of methylene chloride. The aqueous layer is extracted with methylene chloride and the combined organic extract dried, filtered, acidified with hydrochloric acid/methanol and concentrated in vacuo. The residue is twice recrystallized from hot acetonitrile/methanol to afford a white solid, M.P. 193°-194.5° C.

Workup

  1. stirringstirring continued 45 minutes
  2. stirringstirring
  3. waitcontinued for 48 hrs
  4. filtrationThe reaction mixture is filtered
  5. concentrationconcentrated in vacuo
  6. customThe resultant yellow solid is partitioned between 150 ml of water and 125 ml of methylene chloride
  7. extractionThe aqueous layer is extracted with methylene chloride
  8. extractionthe combined organic extract
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue is twice recrystallized from hot acetonitrile/methanol
  13. customto afford a white solid, M.P. 193°-194.5° C.

Sources & evidence

ORD record
ord-03113cf3255e44bdb998d0160a6d490f
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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