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Benzyl Bromide → N-Benzyl-N-(2-bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

HRID 1716279
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인쇄 미리보기

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HRID 1716279 반응식
[Br:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C=O)C.CCOC(C)=O.O>[CH2:31]([N:8]([C:7]1[C:2]([Br:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86619931N-(2-Bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

생성물 1

HCID 86619932N-Benzyl-N-(2-bromo-pyridin-3-yl)-4-phenoxy-benzenesulfonamide

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of N-(2-bromo-pyridin-3-yl)-4-phenoxy-benzene-sulfonamide (0.38 g, 0.94 mmol) from step A and K2CO3 (0.39 g, 2.81 mmol) in dry DMF (10 mL) was added benzylbromide (0.13 mL, 1.13 mmol). The resulting mixture was heated at 80 C overnight. The cooled reaction was diluted with EtOAc and water. The aqueous layer was extracted with EtOAc (×3) and the combined organics were washed with water and brine, dried over anhydrous Na2SO4, and filtered through Celite. The filtrate was concentrated under the reduced pressure and purified by chromatography (silica gel, 25% EtOAc/hexanes). MS: 495, 497 (M+H)+.

후처리

  1. temperatureThe resulting mixture was heated at 80 C overnight
  2. customThe cooled reaction
  3. extractionThe aqueous layer was extracted with EtOAc (×3)
  4. washthe combined organics were washed with water and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered through Celite
  7. concentrationThe filtrate was concentrated under the reduced pressure
  8. custompurified by chromatography (silica gel, 25% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-a5e6b819d4894836bc7d8f888827d806
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803793B2

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