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

HRID 55963노트

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HRID 55963 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0ae58a7bea9b448d94080ecb9f4afef9
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434688B2

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