Methanesulfonyl chloride → 2,5-Difluoro-4-cyano-1-methanesulfonylaminobenzene

HRID 656268ノート

反応式

HRID 656268 の反応式
[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.C([Li])CCC.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>O1CCCC1>[F:10][C:9]1[CH:8]=[C:5]([C:6]#[N:7])[C:4]([F:11])=[CH:3][C:2]=1[NH:1][S:18]([CH3:17])(=[O:20])=[O:19]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 27359004-Amino-2,5-difluorobenzonitrileHCID 178418339Butyllithium

生成物 1

HCID 691185102,5-Difluoro-4-cyano-1-methanesulfonylaminobenzene収率 79.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To an ice-cold solution of 4-amino-2,5-difluorobenzonitrile (1.0 g) in anhydrous tetrahydrofuran (50 ml) was slowly added n-butyl lithium (2.6 ml) through an injector with stirring, followed by stirring 30 minutes. To the mixture was slowly added methanesulfonyl chloride (550 μl), followed by stirring at room temperature for 24 hours. After confirming the completion of the reaction using TLC, the resulting mixture was concentrated under reduced pressure, diluted with 1 N aqueous hydrochloric acid (100 ml), extracted with dichloromethane (50 ml×3). The combined organic layer was dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. The obtained residue was purified by column-chromatography (ethyl acetate/hexane 2/3) to yield 2,5-difluoro-4-cyano-1-methanesulfonylaminobenzene (1.2 g, 79.6%).

後処理

  1. stirringby stirring 30 minutes
  2. stirringby stirring at room temperature for 24 hours
  3. concentrationthe resulting mixture was concentrated under reduced pressure
  4. additiondiluted with 1 N aqueous hydrochloric acid (100 ml)
  5. extractionextracted with dichloromethane (50 ml×3)
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by column-chromatography (ethyl acetate/hexane 2/3)

出典と根拠

ORDレコード
ord-6d3f4c4c46da4cba80ec6a1c0148dd96
出典データセット
uspto-grants-2011_12
特許番号
US08071650B2

反応ノート

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