1,2-Diaminocyclohexane, trans- → 1-(4-Methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-one

HRID 80040

反応式

HRID 80040 の反応式
N[C@@H]1CCCC[C@H]1N.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH3:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N:24]1[CH2:28][CH2:27][NH:26][C:25]1=[O:29].Br[C:31]1[S:32][C:33]([CH3:36])=[CH:34][CH:35]=1>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[CH3:17][C:18]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N:24]1[CH2:28][CH2:27][N:26]([C:31]2[S:32][C:33]([CH3:36])=[CH:34][CH:35]=2)[C:25]1=[O:29]

参加物

9

反応物 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 698312-Bromo-5-methylthiopheneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

生成物 1

HCID 498718671-(4-Methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-one収率 74%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

Copper iodide (16 mg, 0.084 mmol), trans-1,2-diamino cyclohexane (28.8 mg, 0.25 mmol) and potassium phosphate (445 mg, 2.1 mmol) were added to 1,4-Dioxane (10 mL) previously degassed with argon (10 minutes). The reaction mixture was purged with argon for a further 10 minutes, followed by the addition of 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.84 mmol) and 2-bromo-5-methylthiophene (150 mg, 0.84 mmol). The resulting mixture was heated to reflux at 110° C. for 4 hours. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was filtered through celite and the celitebed was washed with chloroform. The organic layer was dried over Na2SO4 and concentrated. The concentrate was quenched with ice, the precipitate formed was collected and dried to afford 170 mg (74% yield) of 1-(4-methyl-pyridin-3-yl)-3-(5-methyl-thiophen-2-yl)-imidazolidin-2-one.

後処理

  1. custompreviously degassed with argon (10 minutes)
  2. customThe reaction mixture was purged with argon for a further 10 minutes
  3. temperatureThe resulting mixture was heated
  4. filtrationThe reaction mixture was filtered through celite
  5. washthe celitebed was washed with chloroform
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customThe concentrate was quenched with ice
  9. customthe precipitate formed
  10. customwas collected
  11. customdried

出典と根拠

ORDレコード
ord-9d155cf1125b484f9d5ab50ed4b67e28
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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