Dimethyl Sulfoxide → 4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

HRID 2286740Notes

Reaction equation

HRID 2286740 reaction equation
[C:1](S(O)=O)([NH2:3])=[NH:2].[H-].[Na+].[Na].N[CH2:11][CH2:12]S.[CH3:14][O-].[Na+].Cl.Cl.[NH2:19][CH2:20]CS.[CH3:23][S:24]([CH3:26])=O>O.CO>[NH2:19][CH2:20][CH2:23][S:24][CH2:26][C:14]1[N:2]=[CH:1][NH:3][C:11]=1[CH3:12]

Participants

10

Reactant 7

HCID 679Dimethyl SulfoxideHCID 6058CysteamineHCID 24758Sodium hydrideHCID 61274Thiourea dioxideHCID 5360545SodiumHCID 101541332-aminoethanethiol DihydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazole

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Triphenyl β-acetylvinylphosphonium bromide (4.11 g., 0.01 mole) was added in one portion to a stirred suspension of 1.1 g. (0.01 mole) of formamidine sulfinic acid in 20 ml. of dimethylsulfoxide containing 0.25 g. of sodium hydride. The mixture was stirred at ambient temperature for 1 hour then at 80° for an additional hour. A solution of 0.99 g. (0.01 mole) of the sodium salt of cysteamine, prepared by addition of two equivalents of sodium methoxide to cysteamine dihydrochloride, in 10 ml. of methanol was added and the resulting mixture was heated at 70°-80° for 4 hours. The mixture was diluted with twice its volume of water and the triphenyl phosphine was removed by filtration. The filtrate was extracted with 100 ml. of toluene and with two 100 ml. portions of chloroform. The chloroform extracts were combined, dried (MgSO4) and evaporated to dryness to give 4-(2-aminoethyl)thiomethyl-5-methylimidazole.

Workup

  1. waitat 80° for an additional hour
  2. temperaturethe resulting mixture was heated at 70°-80° for 4 hours
  3. customthe triphenyl phosphine was removed by filtration
  4. extractionThe filtrate was extracted with 100 ml
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6575deb9d3d24334bad58998b8e773a5
Source dataset
uspto-grants-1981_05
Patent number
US04267337

Reaction notes

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