Potassium Phosphate, Tribasic → 4-(2-Methyl-4-nitrophenyl)-1,4-oxazepan-5-one

HRID 218527ノート

反応式

HRID 218527 の反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[O:9]1[CH2:15][CH2:14][C:13](=[O:16])[NH:12][CH2:11][CH2:10]1.I[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][C:19]=1[CH3:27].CN(C)CCN>[Cu]I.O1CCOCC1>[CH3:27][C:19]1[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=1[N:12]1[C:13](=[O:16])[CH2:14][CH2:15][O:9][CH2:10][CH2:11]1

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 66053N,N-DimethylethylenediamineHCID 792252-Iodo-5-nitrotolueneHCID 70230201,4-Oxazepan-5-one

生成物 1

HCID 595867304-(2-Methyl-4-nitrophenyl)-1,4-oxazepan-5-one

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

3.32 g (15.6 mmol) of potassium phosphate are mixed with 0.5 g (2.6 mmol) of copper(I) iodide in a round-bottom flask, and baked out and filled with argon in repeated alternation. Subsequently, 10 ml of anhydrous dioxane, 1.5 g (13.0 mmol) of 1,4-oxazepan-5-one, 3.43 g (13.0 mmol) of 1-iodo-2-methyl-4-nitrobenzene and 0.46 g (5.21 mmol) of N,N-dimethylethylenediamine are added, and the mixture is heated to 110° C. for 15 h. The mixture is allowed to cool and filtered through silica gel, and the silica gel is washed with dioxane. The combined filtrates are concentrated to dryness under reduced pressure. The residue is dissolved in acetonitrile and purified by preparative HPLC with a gradient of water and acetonitrile. The product fractions are combined and concentrated to dryness under reduced pressure. This affords 430 mg (13% of theory) of the desired product.

後処理

  1. additionfilled with argon in repeated alternation
  2. temperatureto cool
  3. filtrationfiltered through silica gel
  4. washthe silica gel is washed with dioxane
  5. concentrationThe combined filtrates are concentrated to dryness under reduced pressure
  6. dissolutionThe residue is dissolved in acetonitrile
  7. custompurified by preparative HPLC with a gradient of water and acetonitrile
  8. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-81e35fe8f72c40a28cb1812900cc756b
出典データセット
uspto-grants-2012_06
特許番号
US08198267B2

反応ノート

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