Triethylamine → HCID 54094150, compound

HRID 2295009Notes

Reaction equation

HRID 2295009 reaction equation
C(N(CC)CC)C.[CH2:8]([C:10](=[CH:15][CH:16]([CH3:18])[CH3:17])[CH:11]=[CH:12][CH2:13][NH2:14])[CH3:9].Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1>ClCCl>[CH2:8]([C:10](=[CH:15][CH:16]([CH3:17])[CH3:18])[CH:11]=[CH:12][CH2:13][NH:14][C:20]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[O:27])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 54417124HCID 54417124, compound

Product 1

HCID 54094150HCID 54094150, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of triethylamine (5.06 g) and 4-ethyl-6-methyl-2,4-heptadiene-1-ylamine (3.06 g) in dichloromethane (50 ml) at 0° C. was added nicotinic acid chloride hydrochloride (3.56 g) in small portions during 5 minutes. The mixture was stirred for 30 minutes at 0° C. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was dissolved in isopropyl ether (20 ml) and allowed to stand at 5° C. overnight to give 4.46 g of N-(4-ethyl-6-methyl-2,4-heptadiene-1-yl)-3-pyridinecarboxamide.

Workup

  1. washThe reaction mixture was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated in vacuo
  4. dissolutionThe residue was dissolved in isopropyl ether (20 ml)
  5. waitto stand at 5° C. overnight

Sources & evidence

ORD record
ord-5355e833592945678fee4cb2cf2913e7
Source dataset
uspto-grants-1997_11
Patent number
US05691366

Reaction notes

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