Octadecylamine → N-octadecyl-o-iodobenzamide

HRID 1277909

Reaction equation

HRID 1277909 reaction equation
[CH2:1]([NH2:19])[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][CH2:16][CH2:17][CH3:18].[I:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24].Cl.C(N)CCCCCCCCCCCCCCCCC>CCOCC.C(O)C>[CH2:1]([NH:19][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=1[I:20])[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][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 15793OctadecylamineHCID 691122-Iodobenzoyl chlorideHCID 519552Stearamine hydrochloride

Product 1

HCID 13020107N-octadecyl-o-iodobenzamideYield 8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 17.9 g of octadecylamine in a mixture of 300 ml of ether and 10 ml of ethanol was reacted with a solution of 8.0 g of o-iodobenzoyl chloride in 25 ml of ether for 10 minutes. The precipitate which formed contained octadecylamine hydrochloride. This precipitate was recovered and discarded. The volume was thereafter reduced to approximately half at 65° on a water bath. The resulting precipitate was recovered in accordance with the procedure of Example 3. The crude product was recrystallized from benzene to yield 1.2 g of N-octadecyl-o-iodobenzamide as a white microcrystalline solid, m.p. 94°-96°, Rf 0.77.

Workup

  1. customThe precipitate which formed
  2. customThis precipitate was recovered
  3. customThe volume was thereafter reduced to approximately half at 65° on a water bath
  4. customThe resulting precipitate was recovered in accordance with the procedure of Example 3
  5. customThe crude product was recrystallized from benzene

Sources & evidence

ORD record
ord-47dc18bce46f4196a740298cca09af88
Source dataset
uspto-grants-1981_07
Patent number
US04279887

Linked notes

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