Methanesulfonyl chloride → N-(4-Cyano-2-iodo-5-(trifluoromethyl)phenyl)methanesulfonamide

HRID 646581ノート

反応式

HRID 646581 の反応式
[NH2:1][C:2]1[C:9]([I:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.CC(C)([O-])C.[K+].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[C:6]([C:5]1[C:4]([C:11]([F:14])([F:12])[F:13])=[CH:3][C:2]([NH:1][S:22]([CH3:21])(=[O:24])=[O:23])=[C:9]([I:10])[CH:8]=1)#[N:7]

参加物

5

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 23665647Potassium tert-butoxideHCID 250673774-Amino-5-iodo-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 21091191N-(4-Cyano-2-iodo-5-(trifluoromethyl)phenyl)methanesulfonamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

4-Amino-5-iodo-2-trifluoromethyl-benzonitrile (8.04 g, 25.77 mmoles) was dissolved in anhydrous THF (60 mL), stirred under a nitrogen atmosphere and cooled in an ice/brine bath for 20 min. 1.0 M potassium tert-butoxide in THF (82 mL, 82 mmoles) was added and the reaction mixture was stirred for 20 min. Methanesulfonyl chloride (3.2 mL, 41.18 mmoles) was then added and the reaction mixture was stirred at ambient temperature overnight. The reaction mixture was quenched with 1N HCl (90 mL) and extracted with dichloromethane (3×100 mL). The organic extracts were diluted with diethyl ether and a white solid precipitated. The solid was filtered, washed and dried to yield the title compound. The filtrate was concentrated to a crude orange solid. The compound was purified by column chromatography (SiO2, 100% CH2Cl2).

後処理

  1. temperaturecooled in an ice/brine bath for 20 min
  2. stirringthe reaction mixture was stirred for 20 min
  3. stirringthe reaction mixture was stirred at ambient temperature overnight
  4. customThe reaction mixture was quenched with 1N HCl (90 mL)
  5. extractionextracted with dichloromethane (3×100 mL)
  6. additionThe organic extracts were diluted with diethyl ether
  7. customa white solid precipitated
  8. filtrationThe solid was filtered
  9. washwashed
  10. customdried

出典と根拠

ORDレコード
ord-502b86893fe5449d8ae58fdaba6d58fa
出典データセット
uspto-grants-2010_04
特許番号
US07705147B2

反応ノート

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