Methyl iodide → Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

HRID 2071118ノート

反応式

HRID 2071118 の反応式
[H-].[Na+].[CH3:3][S:4]([NH:7][C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:6])=[O:5].I[CH3:23]>CN(C=O)C>[CH3:23][N:7]([C:8]1[CH:9]=[C:10]([C:18]([O:20][CH3:21])=[O:19])[CH:11]=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14])[S:4]([CH3:3])(=[O:6])=[O:5]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3711983Dimethyl 5-(methylsulfonamido)isophthalate

生成物 1

HCID 11324067Dimethyl 5-(N-methylmethylsulfonamido)isophthalate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred suspension of NaH (0.24 g, 10 mmol, 60% in oil dispersion) in 10 mL of DMF was added dimethyl 5-(methylsulfonamido)isophthalate (1.435 g, 5 mmol) followed by iodomethane (0.62 mL, 10 mmol) at room temperature. After 5 h, the reaction was quenched by H2O (25 mL). Then the reaction mixture was extracted with EtOAc, further washed with H2O to remove excess of DMF, dried over anhydrous Na2SO4 and concentrated. The crude product thus obtained was washed with hexanes to give dimethyl 5-(N-methylmethylsulfonamido)isophthalate as a white solid in 91% (1.37 g) yield.

後処理

  1. customthe reaction was quenched by H2O (25 mL)
  2. extractionThen the reaction mixture was extracted with EtOAc
  3. washfurther washed with H2O
  4. customto remove excess of DMF
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe crude product thus obtained
  8. washwas washed with hexanes

出典と根拠

ORDレコード
ord-8d7e507390404a2e8d7badc1f9135198
出典データセット
uspto-grants-2012_10
特許番号
US08299267B2

反応ノート

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