Water → N-Hexadecyl-3-pyridinecarboxamide

HRID 2285763Notes

Reaction equation

HRID 2285763 reaction equation
[CH2:1]([NH2:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].N1C=CC=CC=1.Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1.O>C(#N)C>[CH2:1]([NH:17][C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962Water2×HCID 1049PyridineHCID 8926HexadecylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)

Product 1

HCID 459514N-Hexadecyl-3-pyridinecarboxamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

30.7 g of cetylamine and 33.2 g of pyridine were dispersed in 200 ml of acetonitrile, and 25 g of nicotinic acid chloride hydrochloride was added thereto under cooling with water. After reacting for 3 hours at 55° C., 800 ml of water was added thereto. The thus formed crystals were collected by filtration. Recrystallization from 500 ml of ethanol yielded 36.3 g of the end product. m.p. 85°-87° C.

Workup

  1. filtrationThe thus formed crystals were collected by filtration
  2. customRecrystallization from 500 ml of ethanol

Sources & evidence

ORD record
ord-25c9654cff3a4d99b38997d25be60e4f
Source dataset
uspto-grants-1982_04
Patent number
US04324855

Reaction notes

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