Bromine → N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide

HRID 251829노트

반응식

HRID 251829 반응식
[Br:1]Br.[C:3]([C:6]1[CH:7]=[C:8]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=[C:10]([C:12]#[N:13])[CH:11]=1)(=[O:5])[CH3:4]>CCOCC>[Br:1][CH2:4][C:3]([C:6]1[CH:7]=[C:8]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])[CH:9]=[C:10]([C:12]#[N:13])[CH:11]=1)=[O:5]

참가 물질

4

반응물 2

HCID 24408BromineHCID 57686801N-(3-acetyl-5-cyanophenyl)methanesulfonamide

생성물 1

HCID 57686827N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide수율 85%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Al(CH3)3 (20 mmol) was added dropwise to the ice-water cooled solution of DMEDA (4.4 mmol) in dry toluene (60 mL) under nitrogen. After addition, it was continued to stir for 2 hours at room temperature. Then, methyl-3-cyano-5-(methylsulfonamido)benzoate (4 mmol) was added, and the reaction mixture was heated to reflux overnight. After cooling, it was poured into diluted hydrochloric acid, the mixture was extracted with EtOAc, the combined organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated to afford N-(3-acetyl-5-cyanophenyl)methanesulfonamide with a yield of 35%. Br2 (1.2 mmol) was added dropwise to the solution of N-(3-acetyl-5-cyanophenyl)methanesulfonamide (1 mmol) in Et2O (50 mL). After addition, it was continued to stir for 1.5 hours. Then the reaction mixture was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated to afford N-(3-(2-bromoacetyl)-5-cyanophenyl)methanesulfonamide with a yield of 85%.

후처리

  1. additionAfter addition, it
  2. washThen the reaction mixture was washed with water and brine sequentially
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c0d48d462191431388f872acdbbcc501
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868001B2

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