Dimethyl Sulfate → (2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 376037

反応式

HRID 376037 の反応式
[OH:1]/[N:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:4]([NH:6][CH3:7])=[O:5].[C:21](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O.[OH-].[Na+]>C1(C)C=CC=CC=1.CC(C)=O>[CH3:21][O:1]/[N:2]=[C:3](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)/[C:4]([NH:6][CH3:7])=[O:5]

参加物

7

反応物 4

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 9816878(E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide

生成物 1

HCID 5483872(2E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide収率 94.4%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 1140Toluene溶媒

実験手順

To E-2-hydroxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide (10.00 g, 0.037 mole) were added acetone (200 ml), potassium carbonate (15.34 g, 0.111 moles) and dimethylsulfate (9.33 g, 0,074 moles) and the mixture was stirred at room temperature for 9 hours. After completion of the reaction, the reaction mixture was filtered, washed with acetone and concentrated under reduced pressure. The oil thus obtained was dissolved in toluene (50 ml) and to this was added an aqueous 1N sodium hydroxide solution (50 ml), followed by stirring at room temperature for 30 minutes. The mixture was extracted with toluene, washed with water and concentrated, and then the resulting residue was recrystallized (methanol/water) to obtain E-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide (9.93 g, yield: 94.4%) as colorless crystals (melting point: 81.5°-83° C.).

後処理

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. washwashed with acetone
  4. concentrationconcentrated under reduced pressure
  5. customThe oil thus obtained
  6. stirringby stirring at room temperature for 30 minutes
  7. extractionThe mixture was extracted with toluene
  8. washwashed with water
  9. concentrationconcentrated
  10. customthe resulting residue was recrystallized (methanol/water)

出典と根拠

ORDレコード
ord-df680024924a45c39dbde757034b9732
出典データセット
uspto-grants-1996_01
特許番号
US05488159

関連ノート

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