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

HRID 1928961노트

반응식

HRID 1928961 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1eea11beb50649cfae9dd68ebbb4a329
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08183273B2

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