Methanol → HCID 12143940、化合物

HRID 2113779ノート

反応式

HRID 2113779 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 12143940HCID 12143940、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4d7fbf78060f446697e2fe0821d2a78c
出典データセット
uspto-grants-2008_10
特許番号
US07432283B2

反応ノート

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