Triethylamine → 4,4,5-Trimethyl-2-(2-nitro-4-methylsulfonylbenzoyl)cyclohexane-1,3-dione

HRID 2108243ノート

反応式

HRID 2108243 の反応式
[CH3:1][C:2]1([CH3:11])[CH:7]([CH3:8])[CH2:6][C:5](=[O:9])[CH2:4][C:3]1=[O:10].C(N(CC)CC)C.[N+:19]([C:22]1[CH:30]=[C:29]([S:31]([CH3:34])(=[O:33])=[O:32])[CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25])([O-:21])=[O:20].[C-]#N.[K+]>C(Cl)Cl.C(#N)C>[CH3:11][C:2]1([CH3:1])[CH:7]([CH3:8])[CH2:6][C:5](=[O:9])[CH:4]([C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:29]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:30][C:22]=2[N+:19]([O-:21])=[O:20])[C:3]1=[O:10]

参加物

7

反応物 4

HCID 8471Triethylamine2 回HCID 9032Potassium CyanideHCID 148001864-(Methanesulfonyl)-2-nitrobenzoyl chlorideHCID 148237354,4,5-Trimethyl-cyclohexane-1,3-dione

生成物 1

HCID 148237364,4,5-Trimethyl-2-(2-nitro-4-methylsulfonylbenzoyl)cyclohexane-1,3-dione収率 23.5%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

4,4,5-trimethyl-cyclohexane-1,3-dione (0.98 g, 6.36 mmole) and triethylamine (0.77 g, 7.26 mmole) were dissolved in methylene chloride (30 ml). Into the resulting solution cooled with ice, a methylene chloride solution (5 ml) of 2-nitro-4-methylsulfonylbenzoyl chloride (1.68 g, 6.38 mmole) was dropped, and then this solution was stirred at room temperature for an hour. The resulting solution was washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in acetonitrile (40 ml), into which triethylamine (0.77 g, 7.62 mmole) and potassium cyanide (0.1 g, 1.54 mmole) were added to stir at room temperature for 16 hours. The reaction solution was concentrated under reduced pressure. The residue was dissolved by adding ethyl acetate and water. To the resulting solution, diluted hydrochloric acid was added until the aqueous layer became acidic (pH 2 or below). The organic layer was washed with water, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Methanol was added to the residue to crystallize to give crystal (0.57 g, mp: 166°-7° C.).

後処理

  1. temperatureInto the resulting solution cooled with ice
  2. washThe resulting solution was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionwere added
  6. stirringto stir at room temperature for 16 hours
  7. concentrationThe reaction solution was concentrated under reduced pressure
  8. dissolutionThe residue was dissolved
  9. additionby adding ethyl acetate and water
  10. additionTo the resulting solution, diluted hydrochloric acid was added until the aqueous layer
  11. washThe organic layer was washed with water
  12. dry with materialdried with anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. additionMethanol was added to the residue
  15. customto crystallize

出典と根拠

ORDレコード
ord-8d7e25df7f72472fb41efbf28afd6f54
出典データセット
uspto-grants-1990_06
特許番号
US04937386

反応ノート

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