4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 13646625, compound

HRID 1979738Notes

Reaction equation

HRID 1979738 reaction equation
CS([C:4]1[NH:5][CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[N+:9]([O-:11])=[O:10])=O.[CH3:18][C:19]1[NH:23][CH:22]=[N:21][C:20]=1[CH2:24][S:25][CH2:26][CH2:27][NH2:28]>C(O)C>[CH3:18][C:19]1[NH:23][CH:22]=[N:21][C:20]=1[CH2:24][S:25][CH2:26][CH2:27][NH:28][C:4]1[NH:5][CH:6]=[C:7]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:8]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 13646633HCID 13646633, compound

Product 1

HCID 13646625HCID 13646625, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Methylsulphinyl-3-nitro-4-phenylpyrrole (2.0 g, 0.008 mol) was partially dissolved in ethanol (150 ml) and a solution of 2-(5-methyl-4-imidazolylmethylthio)ethylamine (1.37 g, 0.008 mol) in a little ethanol was added to it. The mixture was refluxed for seven days, after which the mixture was stripped and chromatographed on a silica gel column, collecting the required product by elution with ethyl acetate. The crude solid was recrystallised from 2-propanol to give 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-3-nitro-4-phenylpyrrole (0.46 g), m.p. 182°-184°.

Workup

  1. temperatureThe mixture was refluxed for seven days
  2. customchromatographed on a silica gel column
  3. customcollecting the required product
  4. washby elution with ethyl acetate
  5. customThe crude solid was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-b383751aae004b97b708796012c96e65
Source dataset
uspto-grants-1984_11
Patent number
US04482563

Reaction notes

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