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

HRID 400587

반응식

HRID 400587 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-53ca051e0a414058a5925be0c353bd28
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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