Sodium Hydroxide → HCID 178516266, compound

HRID 569906Notes

Reaction equation

HRID 569906 reaction equation
Cl.Cl.[CH2:3]([NH:10][NH2:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].CN([CH:17]=[C:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24])C>CO>[CH2:3]([NH:10][NH:11][CH:17]=[C:18]1[C:22](=[O:23])[CH2:21][CH2:20][C:19]1=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 146540Benzylhydrazine dihydrochlorideHCID 6433682-[(dimethylamino)methylene]cyclopentane-1,3-dione

Product 1

HCID 178516266HCID 178516266, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 1.3 grams of benzylhydrazine dihydrochloride and 2.8 ml of 5 N sodium hydroxide in 10 ml of methanol was added to an ice-cold solution of 2-dimethylaminomethylene-1,3-cyclopentanedione in 20 ml of methanol. The mixture was heated at reflux for 2 hours and concentrated under reduced pressure. The residue was extracted several times with dichloromethane and the combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure to give a fluffy yellow solid. This was recrystallized from a mixture of toluene and hexane to give 2-[(2-benzylhydrazino)methylene]-1,3-cyclopentanedione melting about 164° C. with decomposition.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. concentrationconcentrated under reduced pressure
  4. extractionThe residue was extracted several times with dichloromethane
  5. dry with materialthe combined dichloromethane extracts were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give a fluffy yellow solid
  8. customThis was recrystallized from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-a6a007fc16644247ab5f1a21ab65376c
Source dataset
uspto-grants-1988_03
Patent number
US04734430

Reaction notes

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