4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 178485004, compound

HRID 354532Notes

Reaction equation

HRID 354532 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](=[N:19][CH3:20])[S:15]([O-:18])(=[O:17])=[O:16]>C(#N)C>[CH3:20][NH:19][C:14]([S:15]([OH:18])(=[O:17])=[O:16])=[N:11][CH2:10][CH2:9][S:8][CH2:7][C:3]1[N:4]=[CH:5][NH:6][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 867370781-Methylthio-1-methyliminomethanesulphonate

Product 1

HCID 178485004HCID 178485004, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 1.43 g (0.0085 mole) of 2-(5-methyl-4-imidazolylmethylthio)ethylamine in dry acetonitrile (150 ml) was added dropwise, with stirring, to a solution of 1.43 g (0.0084 mole) of 1-methylthio-1-methyliminomethanesulphonate in dry acetonitrile (150) at 50°, giving an immediate white precipitation. After further warming at 70° for one hour, the mixture was stripped to dryness, dissolved in methanol and absorbed onto silica gel. Chromatography on a column of silica gel was performed with ethylacetate/methanol (20:1), and the crude product recrystallised from isopropanol to give the title compound, 0.46 g.m.p. 162.5°-163.5° as an almost colourless crystalline solid.

Workup

  1. customgiving
  2. customan immediate white precipitation
  3. temperatureAfter further warming at 70° for one hour
  4. dissolutiondissolved in methanol
  5. customabsorbed onto silica gel
  6. customthe crude product recrystallised from isopropanol

Sources & evidence

ORD record
ord-1b0e38f1095443ceb7f18e44de0cdbfa
Source dataset
uspto-grants-1983_03
Patent number
US04375472

Reaction notes

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