Water → 3-Methyl-4-[[(1-methylimidazol-2-yl)methyl]sulfanyl]aniline

HRID 856762

Reaction equation

HRID 856762 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([CH3:9])[CH:3]=1.[OH-].[Na+].Cl.Cl[CH2:14][C:15]1[N:16]([CH3:20])[CH:17]=[CH:18][N:19]=1.O>CO>[CH3:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[S:8][CH2:14][C:15]1[N:16]([CH3:20])[CH:17]=[CH:18][N:19]=1)[NH2:1]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideHCID 198673854-Amino-2-methylbenzene-1-thiol

Product 1

HCID 433031753-Methyl-4-[[(1-methylimidazol-2-yl)methyl]sulfanyl]anilineYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 4-amino-2-methylthiophenol (500 mg) in methanol (10 ml) was added 1N aqueous solution of sodium hydroxide (12 ml), and a solution of 2-chloromethyl-1-methylimidazole hydrochloride (660 mg) in methanol (10 ml) was added at 0° C. Water was added to the mixture, and the mixture was extracted with ethyl acetate and the organic layer was dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was recrystallized from hexane-ethyl acetate, to give 3-methyl-4-[[(1-methylimidazol-2-yl)methyl]sulfanyl]aniline (757 mg) as crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe obtained residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ae67017008b04a2f986cd7277017ef2c
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Linked notes

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