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

HRID 21662

Reaction equation

HRID 21662 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].ClC[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.[CH2:23](N(CC)CC)C>CS(C)=O.CCOCC>[C:1]([N:5]([CH3:23])[N:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[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

6

Reactant 3

HCID 8471TriethylamineHCID 23393Picolyl chlorideHCID 299436N'-tert-butylbenzohydrazide

Product 1

HCID 19368177N'-t-butyl-N-benzoyl-N'-methylpyridinylhydrazineYield 20%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

N'-t-butyl-N-benzoyl hydrazine (1.2 g), 2-chloromethyl pyridine (1.0 g) and triethylamine (2 equivalents) were stirred in dimethyl sulfoxide (15 ml) at room temperature for 2 hours. The reaction mixture was then warmed to 50° C. for 2 hours. The mixture was diluted with ether and washed with water. The organic layer was dried over magnesium sulfate, filtered and rotavapped to afford a yellow oil. The oil was chromatographed on silica gel (G:70-230 mesh) using a methylene chloride-ether mixture (1:1) as eluant to afford the purified product as a yellow gum in approximately 20% yield.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customto afford a yellow oil
  5. customThe oil was chromatographed on silica gel (G:70-230 mesh)

Sources & evidence

ORD record
ord-682d8d43834e4d31a8179b4d5b542b64
Source dataset
uspto-grants-1995_06
Patent number
US05424333

Linked notes

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