4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 12831748, compound

HRID 542186Notes

Reaction equation

HRID 542186 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH2:11].CS[C:14]1[NH:15][CH2:16][CH2:17][CH2:18][C:19]=1[N+:20]([O-:22])=[O:21]>C(O)C>[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH2:7][S:8][CH2:9][CH2:10][NH:11][C:14]1[NH:15][CH2:16][CH2:17][CH2:18][C:19]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 12831745HCID 12831745, compound

Product 1

HCID 12831748HCID 12831748, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(5-methyl-4-imidazolylmethylthio)ethylamine (0.51 g, 0.003 mol) and 2-methylthio-3-nitro-1,4,5,6-tetrahydropyridine (0.49 g, 0.003 mol) in ethanol (50 ml) was refluxed for 6 hours. The mixture was cooled, and the solvent was removed in vacuo. The residue was dissolved in hot propan-2-ol and the product crystallised on cooling. Recrystallisation of the product from propan-2-ol/methanol gave 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-3-nitro-1,4,5,6-tetrahydropyridine (0.66 g, 82%) m.p. 205.5°-206.5°.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in hot propan-2-ol
  4. customthe product crystallised
  5. temperatureon cooling
  6. customRecrystallisation of the product from propan-2-ol/methanol

Sources & evidence

ORD record
ord-f4961a6cba414593a12e5805edd2a1ee
Source dataset
uspto-grants-1987_04
Patent number
US04656176

Reaction notes

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