Cyclooctylamine → HCID 86739195, compound

HRID 2296028Notes

Reaction equation

HRID 2296028 reaction equation
CS[C:3]([NH:8]CCSCC1OC(CN(C)C)=CC=1)=[CH:4][N+:5]([O-:7])=[O:6].[CH:22]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C(O)C>[CH:22]1([NH:30][C:3]([NH2:8])=[CH:4][N+:5]([O-:7])=[O:6])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 2903CyclooctylamineHCID 53427435N-{2-[({5-[(Dimethylamino)methyl]furan-2-yl}methyl)sulfanyl]ethyl}-1-(methylsulfanyl)-2-nitroethen-1-amine

Product 1

HCID 86739195HCID 86739195, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(methylthio)-1-[2-[[[5-(dimethylamino) methyl-2-furanyl]methyl]thio]ethylamino]2-nitroethene (1.05 g, 3.2 mmol) and cyclooctyl amine (1.2 g, 9.5 mmol) in ethanol (20 ml) was stirred at 20° C. for 21 days. The solvent was then removed in vacuo and the residue was chromatographed on a column of alumina (using chloroform as eluant) to give N-[2-[[[5-dimethylamino)-methyl-2-furanyl]methyl]thio]ethyl]-N'-cyclooctyl-2-nitro-1,1-ethenediamine (0.51 g, 39%) as an oil. [NMR τ (CDCl3) -0.30 br (s, 1H), 3.46 (s, 1H), 3.85 (s, 2H), 6.20 (s, 2H), 6.56 (s, 2H), 6.30-6.90 (m, 3H), 7.15-7.30 (m, 2H), 7.75 (s, 6H), 8.00-8.70 (m, 14H)]. [Found [M+H]+ 411.2391; C20H35N4O3S requires [M+H]+ 411.2429.]

Workup

  1. customThe solvent was then removed in vacuo
  2. customthe residue was chromatographed on a column of alumina (using chloroform as eluant)

Sources & evidence

ORD record
ord-25ab1ce45458490f81e64a685a53f442
Source dataset
uspto-grants-1984_01
Patent number
US04427685

Reaction notes

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