2-Methylsulphinyl-3-nitropyrrole → 2-[2-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-3-nitropyrrole

HRID 482656Notes

Reaction equation

HRID 482656 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH2:15])[CH:6]=1)[CH3:3].CS([C:19]1[NH:20][CH:21]=[CH:22][C:23]=1[N+:24]([O-:26])=[O:25])=O>C(O)C>[CH3:3][N:2]([CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([CH2:11][S:12][CH2:13][CH2:14][NH:15][C:19]2[NH:20][CH:21]=[CH:22][C:23]=2[N+:24]([O-:26])=[O:25])[CH:6]=1)[CH3:1]

Participants

4

Reactant 2

HCID 130595162-Methylsulphinyl-3-nitropyrroleHCID 132773272-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamine

Product 1

HCID 147713562-[2-(4-Dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-3-nitropyrroleYield 15%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamine (0.325 g) and 2-methylsulphinyl-3-nitropyrrole (0.25 g) was refluxed in ethanol (12 ml) over 6 days. The solution was evaporated to dryness and the residue was chromatographed on silica gel eluted with 10% methanol/chloroform to give 2-[2-(4-dimethylaminomethyl-2-pyridylmethylthio)ethylamino]-3-nitropyrrole (0.072 g) as a yellow solid m.p. 90°-95° C. dec.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was chromatographed on silica gel
  3. washeluted with 10% methanol/chloroform

Sources & evidence

ORD record
ord-0f634535ded94bd88d6185b6450acdd6
Source dataset
uspto-grants-1986_03
Patent number
US04574126

Reaction notes

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