4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → 1H-PYRROL-2-AMINE, N-[2-[[(5-METHYL-1H-IMIDAZOL-

HRID 1979733Notes

Reaction equation

HRID 1979733 reaction equation
CS([C:4]1[NH:5][CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])=O.[CH3:12][C:13]1[NH:17][CH:16]=[N:15][C:14]=1[CH2:18][S:19][CH2:20][CH2:21][NH2:22]>CO>[CH3:12][C:13]1[NH:17][CH:16]=[N:15][C:14]=1[CH2:18][S:19][CH2:20][CH2:21][NH:22][C:4]1[NH:5][CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 130595162-Methylsulphinyl-3-nitropyrrole

Product 1

HCID 136466221H-PYRROL-2-AMINE, N-[2-[[(5-METHYL-1H-IMIDAZOL-Yield 34.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-methylsulphinyl-3-nitropyrrole (2 g, 0.01 mol) and 2-(5-methyl-4-imidazolylmethylthio)-ethylamine (2 g, 0.01 mol) in methanol (50 ml) was refluxed for 7 days and evaporated to dryness. The residue was chromatographed on a silica gel column eluted with ethyl acetate, and the eluate was evaporated to dryness and recrystallised from propan-2-ol to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-3-nitropyrrole (0.96 g, 31%) m.p. 161°-162°.

Workup

  1. customevaporated to dryness
  2. customThe residue was chromatographed on a silica gel column
  3. washeluted with ethyl acetate
  4. customthe eluate was evaporated to dryness
  5. customrecrystallised from propan-2-ol

Sources & evidence

ORD record
ord-39eaa2f8fbc44489af27a0d071e30b95
Source dataset
uspto-grants-1984_11
Patent number
US04482563

Reaction notes

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