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

HRID 21645

Reaction equation

HRID 21645 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 10N HCl and ether. The layers were separated and the organic layer was washed with 10N 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 as eluant a mixture of 10% CH3OH, 40% CH2Cl2, 50% Et2O 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 10N HCl and ether
  3. customThe layers were separated
  4. washthe organic layer was washed with 10N 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 as eluant
  11. additiona mixture of 10% CH3OH, 40% CH2Cl2, 50% Et2O

Sources & evidence

ORD record
ord-7040c1e3278a4d979435f82d9d30012e
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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