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

HRID 402291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 402291
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-715fbd2a0c74464aa862e5afd37ae5d6
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741943B2

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