Water → 3-Methyl-4-(((1-propylimidazol-5-yl)methyl)sulfanyl)aniline

HRID 402291Notes

Reaction equation

HRID 402291 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([CH3:9])[CH:3]=1.C(N(CC)CC)C.Cl.Cl[CH2:19][C:20]1[N:24]([CH2:25][CH2:26][CH3:27])[CH:23]=[N:22][CH:21]=1.O>O1CCCC1.CO>[CH3:9][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[S:8][CH2:19][C:20]1[N:24]([CH2:25][CH2:26][CH3:27])[CH:23]=[N:22][CH:21]=1)[NH2:1]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 198673854-Amino-2-methylbenzene-1-thiolHCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochloride

Product 1

HCID 661543823-Methyl-4-(((1-propylimidazol-5-yl)methyl)sulfanyl)anilineYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-amino-2-methylthiophenol (500 mg) and triethylamine (3.0 ml) in tetrahydrofuran (15 ml) was added dropwise a solution of 5-chloromethyl-1-propylimidazole hydrochloride (847 mg) in methanol (5 ml) at 0° C. under argon atmosphere, after which the mixture was returned to room temperature and stirred for 3 hours. Water was added and the mixture was extracted with ethyl acetate, and organic layer was washed with saturated brine and dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by basic silica gel column chromatography (hexane:ethyl acetate 1:1→ethyl acetate) and was recrystallized from hexane-ethyl acetate to give 3-methyl-4-[((1-propylimidazol-5-yl)methyl)sulfanyl]aniline (601 mg) as colorless crystals.

Workup

  1. customwas returned to room temperature
  2. extractionthe mixture was extracted with ethyl acetate, and organic layer
  3. washwas washed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resulting residue was purified by basic silica gel column chromatography (hexane:ethyl acetate 1:1→ethyl acetate)
  7. customwas recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-715fbd2a0c74464aa862e5afd37ae5d6
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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