Triethylamine → N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine

HRID 1707668Notes

Reaction equation

HRID 1707668 reaction equation
[C:1]([NH:5][NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([N:5]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[N:19][CH:18]=1)[NH:6][C:7](=[O:14])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 299436N'-tert-butylbenzohydrazide

Product 1

HCID 15767543N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

A solution of N'-t-butyl-N-benzoylhydrazine (2.0 g) and nicotinoyl chloride hydrochloride in 20 ml of methylene chloride at 23° C. was treated dropwise with triethylamine (4 ml). The reaction mixture was stirred at 23° C. for 0.5 hours. Solids were removed by filtration. The filtrate was diluted with N/10 HCl and ether. The layers were separated and the organic layer was washed with N/10 HCl. The aqueous layer was neutralized with solid sodium bicarbonate and extracted with ether. The ether extracts were treated with charcoal and then dried with magnesium sulfate. Evaporation of solvents afforded a yellow oil which was chromatographed on silica gel using 10% CH3OH, 40% CH2Cl2, 50% Et2O as eluant to afford N'-t-butyl-N-benzoyl-N'-nicotinoylhydrazine as a yellow foam. m.p. 60°-63° C.

Workup

  1. customSolids were removed by filtration
  2. additionThe filtrate was diluted with N/10 HCl and ether
  3. customThe layers were separated
  4. washthe organic layer was washed with N/10 HCl
  5. extractionextracted with ether
  6. additionThe ether extracts were treated with charcoal
  7. dry with materialdried with magnesium sulfate
  8. customEvaporation of solvents
  9. customafforded a yellow oil which
  10. customwas chromatographed on silica gel using 10% CH3OH, 40% CH2Cl2, 50% Et2O as eluant

Sources & evidence

ORD record
ord-9b0c8a060e3f461a8d755b17b21a1f8b
Source dataset
uspto-grants-1994_10
Patent number
US05354762

Reaction notes

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