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

HRID 261096

Reaction equation

HRID 261096 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>CO.O>[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-methylimidazoleYield 45%

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 and evaporated to dryness to give 4-(2-aminoethyl)thiomethyl-5-methylimidazole in 45% yield.

Workup

  1. waitat 80° for an additional hour
  2. additionwas added
  3. temperaturethe resulting mixture was heated at 70°-80° for 4 hours
  4. customthe triphenyl phosphine was removed by filtration
  5. extractionThe filtrate was extracted with 100 ml of toluene and with two 100 ml portions of chloroform
  6. customdried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-77e8e0a94005434c9bcf97a7ff593841
Source dataset
uspto-grants-1979_08
Patent number
US04163858

Linked notes

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