Benzenesulfonyl chloride → N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline)

HRID 400587

反応式

HRID 400587 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.[C:10]1([S:16](Cl)(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N([CH2:25][CH3:26])CC)C>ClCCl.C(=O)(O)[O-].[Na+]>[C:10]1([S:16]([N:6]([S:16]([C:26]2[CH:25]=[CH:12][CH:11]=[CH:10][CH:15]=2)(=[O:18])=[O:17])[C:5]2[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][C:4]=2[I:9])(=[O:18])=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 8239344-Bromo-2-iodoaniline

生成物 1

HCID 60026850N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline)収率 35%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of 4-bromo-2-iodoaniline (8.5 g, 28.5 mmol) in 200 mL of dichloromethane was sequentially treated with benzenesulfonyl chloride (15 mL, 117.5 mmol) and triethylamine (25 mL, 179.6 mmol). After 4 days, the mixture was diluted with 100 mL of saturated aqueous sodium bicarbonate solution and extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with 50 mL of brine, three 60 mL portions of saturated aqueous ammonium chloride solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was triturated with diethyl ether to afford 5.74 g (35% yield) of N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline).

後処理

  1. extractionextracted with three 100 mL portions of ethyl acetate
  2. washThe combined organic layers were washed with 50 mL of brine, three 60 mL portions of saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was triturated with diethyl ether

出典と根拠

ORDレコード
ord-53ca051e0a414058a5925be0c353bd28
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

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