Sodium Hydroxide → HCID 178464627, compound

HRID 463783Notes

Reaction equation

HRID 463783 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH2:8]([NH:10][C:11]([NH2:13])=[NH:12])[CH3:9].S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:21][C:22]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:23]=1[CH:24]=[CH:25][C:26](Cl)=[O:27]>O1CCCC1>[ClH:21].[Cl:21][C:22]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:23]=1[CH:24]=[CH:25][C:26]([NH:13][C:11]([NH:10][CH2:8][CH3:9])=[NH:12])=[O:27]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 403983-(2,6-Dichlorophenyl)prop-2-enoyl chlorideHCID 178464632HCID 178464632, compound

Product 1

HCID 178464627HCID 178464627, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 7.48 g of a 50% sodium hydroxide solution, 12.72 g of ethylguanidine sulfate, and 120 ml of tetrahydrofuran is stirred for 45 minutes. Anhydrous sodium sulfate (12 g) is added to the mixture and stirred for 40 minutes. 11.0 g of 2,6-dichlorocinnamoyl chloride in 40 ml of anhydrous tetrahydrofuran are added dropwise to the resulting mixture and stirred overnight. The 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 is dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to a yellow oil. The resulting oil crystallizes on standing. The crystallized solid is dissolved in hot acetonitrile, filtered and recrystallized. The white solid is collected and dried in air, M.P. 166°-171° C.

Workup

  1. stirringstirred for 40 minutes
  2. stirringstirred overnight
  3. filtrationThe reaction mixture is filtered
  4. concentrationconcentrated in vacuo
  5. customthe resulting yellow oil partitioned between 100 ml of methylene chloride and 150 ml of H2O
  6. extractionThe aqueous layer is extracted with methylene chloride
  7. extractionthe combined organic extract
  8. dry with materialis dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo to a yellow oil
  11. customThe resulting oil crystallizes on standing
  12. dissolutionThe crystallized solid is dissolved in hot acetonitrile
  13. filtrationfiltered
  14. customrecrystallized
  15. customThe white solid is collected
  16. customdried in air, M.P. 166°-171° C.

Sources & evidence

ORD record
ord-0cf706e8aa164d1fa0320d94c7aa1670
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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