4-(((2-Aminoethyl)thio)methyl)-5-methylimidazole → HCID 10714370, compound

HRID 568357Notes

Reaction equation

HRID 568357 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].[OH-].[K+].CO.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([S:23]([N:26]=[CH:27]OCC)(=[O:25])=[O:24])=[CH:19][CH:18]=1>CO>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([S:23]([NH:26][CH:27]=[N:11][CH2:10][CH2:9][S:8][CH2:7][C:3]2[N:4]=[CH:5][NH:6][C:2]=2[CH3:1])(=[O:25])=[O:24])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 23689386Potassium hydroxide methanolHCID 53657067HCID 53657067, compound

Product 1

HCID 10714370HCID 10714370, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2.44 g of 2-[[(5-methyl-1H-imidazole-4-yl)methyl]thio]ethanamine (prepared according to British Pat. No. 1,338,169) in 50 ml of methanol, 13.3 ml of 1.45M methanol potassium hydroxide are added at 0° C. To the resulting solution, 2.47 g of ethyl N-p-chlorobenzene-sulphonylformimidate are added at room temperature and stirring. The mixture is kept under stirring for 1 hour at room temperature, then filtered off and the solvent is removed by distillation at reduced pressure. The formed residue is purified by dissolving in 50 ml of ethyl acetate and 25 ml of water. Then, it is acidulated with 3N hydrochloric acid till pH2. The organic phase is cast aside and the aqueous phase is basified in the presence of 50 ml of ethyl acetate with 1N sodium hydroxide till pH8. The organic phase is washed with water, dried over magnesium sulphate and evaporated to dryness. 2.3 g (oily product) of N-p-chlorobenzene-sulphonyl-N'-[2 -[[(5-methyl-1H-imidazole-4-yl)methyl]thio]ethyl]formamidine are obtained.

Workup

  1. stirringunder stirring for 1 hour at room temperature
  2. filtrationfiltered off
  3. customthe solvent is removed by distillation at reduced pressure
  4. customThe formed residue is purified
  5. dissolutionby dissolving in 50 ml of ethyl acetate
  6. washThe organic phase is washed with water
  7. dry with materialdried over magnesium sulphate
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-1b05ad075f304ffdbf090010d2e07885
Source dataset
uspto-grants-1988_03
Patent number
US04728655

Reaction notes

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