Methanol → HCID 12143940、化合物

HRID 916206ノート

反応式

HRID 916206 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-44d7c6f454644111bea41f3dcad6a7f9
出典データセット
uspto-grants-2007_09
特許番号
US07268146B2

反応ノート

読み込み中…