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

HRID 402292Notes

Reaction equation

HRID 402292 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][C:21]=1[CH3:28].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][C:21]=1[CH3:28])[NH2:1]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 198673854-Amino-2-methylbenzene-1-thiolHCID 229385505-Chloromethyl-4-methyl-1-propylimidazole hydrochloride

Product 1

HCID 686500933-Methyl-4-[((4-methyl-1-propylimidazol-5-yl)methyl)sulfanyl]anilineYield 30.4%

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-4-methyl-1-propylimidazole hydrochloride (908 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. The 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) to give 3-methyl-4-[((4-methyl-1-propylimidazol-5-yl)methyl)sulfanyl]aniline (301 mg) as a brown powder.

Workup

  1. customwas returned to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was 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)

Sources & evidence

ORD record
ord-eb87a8ccc5984ecd8effc4155f02d4ad
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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