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

HRID 251829ノート

反応式

HRID 251829 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-c0d48d462191431388f872acdbbcc501
出典データセット
uspto-grants-2011_01
特許番号
US07868001B2

反応ノート

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