5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → 2-[2-(5-Dimethylaminomethyl-2-furylmethylthio)ethylamino]-3-nitropyrrole

HRID 1381007Notes

Reaction equation

HRID 1381007 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])=[CH:7][CH:6]=1)[CH3:3].CS([C:18]1[NH:19][CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])=O>C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[O:9][C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:18]2[NH:19][CH:20]=[CH:21][C:22]=2[N+:23]([O-:25])=[O:24])=[CH:7][CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 130595162-Methylsulphinyl-3-nitropyrrole

Product 1

HCID 136466382-[2-(5-Dimethylaminomethyl-2-furylmethylthio)ethylamino]-3-nitropyrrole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamine (3 g, 0.014 mol) and 2-methylsulphinyl-3-nitropyrrole (2 g, 0.011 mol) in ethanol (50 ml) was refluxed for 7 days, and it was then evaporated to dryness. The residue was purified by elution from a column of silica gel with ethyl acetate-petroleum ether (b.p. 60°-80°) (4:1) to give 2-[2-(5-dimethylaminomethyl-2-furylmethylthio)ethylamino]-3-nitropyrrole, m.p. 67°-67°.

Workup

  1. customit was then evaporated to dryness
  2. customThe residue was purified by elution from a column of silica gel with ethyl acetate-petroleum ether (b.p. 60°-80°) (4:1)

Sources & evidence

ORD record
ord-854e9942f7324899bd93df4de32ef1fc
Source dataset
uspto-grants-1986_04
Patent number
US04584384

Reaction notes

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