Dicyclohexylamine → N,N-Diethyl-5-[6-[(6-bromohexyl)oxy]-1-hexynyl]-2-furancarboxamide

HRID 359747Notes

Reaction equation

HRID 359747 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]([C:6]1[O:7][C:8](Br)=[CH:9][CH:10]=1)=[O:5])[CH3:2].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]#[CH:27].C1(NC2CCCCC2)CCCCC1>>[CH2:1]([N:3]([CH2:12][CH3:13])[C:4]([C:6]1[O:7][C:8]([C:27]#[C:26][CH2:25][CH2:24][CH2:23][CH2:22][O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][Br:14])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 7582DicyclohexylamineHCID 9323705-bromo-N,N-diethyl-2-furamideHCID 218671586-[(6-Bromohexyl)oxy]-1-hexyne

Product 1

HCID 19818694N,N-Diethyl-5-[6-[(6-bromohexyl)oxy]-1-hexynyl]-2-furancarboxamideYield 73.2%

Procedure

N,N-diethyl-5-bromo-2-furancarboxamide (1.5 g) was treated with 6-[(6-bromohexyl)oxy]-1-hexyne (1.59 g) and N,N-dicyclohexylamine (2.10 g) according to the method of Intermediate 9 except that the reaction mixture was refluxed under nitrogen for 3 h and FCC eluting with hexane followed by hexane:ether (4:1→1:1) gave the title compound as an orange oil (1.90 g), t.l.c. (hexane:ether 1:1) Rf 0.15.

Workup

  1. temperaturewas refluxed under nitrogen for 3 h
  2. washFCC eluting with hexane

Sources & evidence

ORD record
ord-fbab3d79d0a742b2b10c46b04de6b4c0
Source dataset
uspto-grants-1991_03
Patent number
US05002966

Reaction notes

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