tert-Butylhydrazine monohydrochloride → HCID 67692469, compound

HRID 1683806Notes

Reaction equation

HRID 1683806 reaction equation
Cl.[C:2]([NH:6][NH2:7])([CH3:5])([CH3:4])[CH3:3].C([O-])(=O)C.[Na+].[Cl:13][C:14]1[CH:29]=[CH:28][C:17]([C:18]([C:20](C)(C)[C:21](OCC)=[O:22])=O)=[CH:16][CH:15]=1>C(O)(=O)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]2[CH2:20][C:21](=[O:22])[N:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[N:7]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 81889tert-Butylhydrazine monohydrochlorideHCID 517045Sodium AcetateHCID 16638375HCID 16638375, compound

Product 1

HCID 67692469HCID 67692469, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

After 1.5 g (12 mmol) of t-butylhydrazine hydrochloride was stirred in 30 ml of acetic acid which contains 0.97 g (12 mmol) of sodium acetate for 30 minutes, 2.0 g (7.9 mmol) of ethyl α-(4-chloro-benzoyl)isobutyrate was added thereto, and the mixture was heated under reflux for 20 hours. Acetic acid was evaporated under reduced pressure, and to the obtained residue was added 50 ml of diethyl ether and 50 ml of water, and then vigorously agitated. The resulting solution was separated, and the aqueous layer was extracted twice with 50 ml of diethyl ether. The organic layer was combined and washed successively with water, 1N hydrochloric acid and saturated brine solution, and dried over anhydrous sodium sulfate. Then the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1 (v/v)) to give 1.4 g of the object compound as white crystals (yield 68%).

Workup

  1. customfor 30 minutes
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 20 hours
  4. customAcetic acid was evaporated under reduced pressure
  5. additionto the obtained residue was added 50 ml of diethyl ether and 50 ml of water
  6. customThe resulting solution was separated
  7. extractionthe aqueous layer was extracted twice with 50 ml of diethyl ether
  8. washwashed successively with water, 1N hydrochloric acid and saturated brine solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThen the solvent was evaporated under reduced pressure
  11. customThe obtained crude product
  12. customwas purified by silica gel column chromatography (n-hexane/ethyl acetate=5/1 (v/v))

Sources & evidence

ORD record
ord-5c12a1d6064642dbaa0d34945325dfd0
Source dataset
uspto-grants-1997_06
Patent number
US05639776

Reaction notes

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