Methanol → HCID 12143940, 화합물

HRID 2113779노트

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HRID 2113779 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C:11]1=[S:16].[C:17](=O)([O:20]C)[O:18][CH3:19].[H-].[Na+].[CH3:25]O>O1CCOCC1>[CH3:19][O:18][C:17]([C:12]1[CH2:13][CH2:14][CH2:15][N:10]([C:3]2[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[Cl:1])[C:11]=1[S:16][CH3:25])=[O:20]

참가 물질

6

반응물 4

HCID 887MethanolHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 121439391-(2-Chloro-4,6-dimethylphenyl)piperidine-2-thione

생성물 1

HCID 12143940HCID 12143940, 화합물

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

1-(2-Chloro-4,6-dimethylphenyl)piperidine-2-thione (5.11 g), dimethyl carbonate (17.0 mL), sodium hydride (3.7 g of a 60% dispersion in mineral oil), and methanol (0.5 mL) were combined in 100 mL of dioxane and the mixture was stirred in a 120° C. oil bath for 4 h. After the reaction had cooled to room temperature, it was quenched by the addition of aqueous ammonium chloride, diluted with water and washed twice with ethyl acetate. After drying over magnesium sulfate, the ethyl acetate was concentrated and the residue chromatographed on silica gel using an acetone/hexane gradient to provide 5.00 g 1-(2-chloro-4,6-dimethylphenyl)-2-methylsulfanyl-1,4,5,6-tetrahydropyridine-3-carboxylic acid methyl ester: mp 85.3-87.6° C.

후처리

  1. temperatureAfter the reaction had cooled to room temperature
  2. customit was quenched by the addition of aqueous ammonium chloride
  3. additiondiluted with water
  4. washwashed twice with ethyl acetate
  5. dry with materialAfter drying over magnesium sulfate
  6. concentrationthe ethyl acetate was concentrated
  7. customthe residue chromatographed on silica gel using an acetone/hexane gradient

출처 및 근거

ORD 기록
ord-4d7fbf78060f446697e2fe0821d2a78c
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432283B2

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