4-Toluenesulfonyl chloride → 5-Methoxy-1-methylimidazolidine-2,4-dione

HRID 1905661ノート

反応式

HRID 1905661 の反応式
[OH:1][CH:2]1[N:6]([CH3:7])[C:5](=[O:8])[NH:4][C:3]1=[O:9].[CH2:10](N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>CO>[CH3:10][O:1][CH:2]1[N:6]([CH3:7])[C:5](=[O:8])[NH:4][C:3]1=[O:9]

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 30362475-Hydroxy-1-methylhydantoin2 回

生成物 1

HCID 123555505-Methoxy-1-methylimidazolidine-2,4-dione収率 68.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

5.0 g of 5-hydroxy-1-methylhydantoin (compound 1) were dissolved in absolute methanol and 6.7 g of triethylamine were added to the solution. 10.9 g (1.5 equivalent) of p-toluenesulfonyl chloride were then added to the solution, and was stirred at room temperature for 3 hours. After the reaction mixture was evaporated to dryness, a small amount of water was added to the residue and was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated to dryness, and the residue was purified by column chromatography on silica gel (ethyl acetate). The obtained crude compound was recrystallized from a mixture of ethyl acetate and hexane to give 3.8 g of 5-methoxy-1-methylhydantoin (compound 5) in the form of white crystals.

後処理

  1. customAfter the reaction mixture was evaporated to dryness
  2. additiona small amount of water was added to the residue
  3. extractionwas extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated to dryness
  6. customthe residue was purified by column chromatography on silica gel (ethyl acetate)
  7. customThe obtained crude compound
  8. customwas recrystallized from a mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-b2d47bb5f1874009a11ae347242dcdbb
出典データセット
uspto-grants-1987_03
特許番号
US04647574

反応ノート

読み込み中…