Benzenesulfonamide, N,4-dimethyl- → N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide

HRID 2077504노트

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HRID 2077504 반응식
[CH3:1][NH:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)(=[O:5])=[O:4].[H-].[Na+].Cl[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[N:17]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C(Cl)Cl.C([O-])(O)=O.[Na+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[Cl:22][C:18]1[N:17]=[C:16]([N:2]([CH3:1])[S:3]([C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=2)(=[O:5])=[O:4])[CH:21]=[CH:20][CH:19]=1

참가 물질

9

반응물 4

HCID 12543Benzenesulfonamide, N,4-dimethyl-HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

생성물 1

HCID 57585115N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide수율 33.7%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 516892Sodium Bicarbonate용매

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온도
100 °C

실험 절차

N-Methyl-p-toluenesulfonamide (0.2 g, 1 mmol) was added to a microwave vial equipped with a stir bar. DMF (3 mL) was added to the mixture, followed by NaH (0.13 g, 5.40 mmol), and the reaction solution was allowed to stir for 20 minutes. Then 2,6-dichloropyridine (0.24 g, 1.6 mmol), palladium(II) acetate (0.0242 g, 0.108 mmol) and Xantphos (0.024 g) were added to the mixture. The vial was capped and placed in the CEM microwave and heated for 10 minutes at 100° C. The mixture was diluted with DCM and saturated NaHCO3. The aqueous layer was extracted with 4:1 DCM/MeOH three times, and the combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude was purified by silica gel chromatography (1-10% EtOAc/hexanes) to give N-(6-chloropyridin-2-yl)-N,4-dimethylbenzenesulfonamide (0.1 g, 31.2% yield) as a colorless oil. MS (ESI pos. ion) m/z: 297 (MH+). Calculated exact mass for C13H13ClN2O2S: 296.

후처리

  1. customvial equipped with a stir bar
  2. customThe vial was capped
  3. extractionThe aqueous layer was extracted with 4:1 DCM/MeOH three times
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude was purified by silica gel chromatography (1-10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ec1ee15e66984335a61881f26d68cd65
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928140B2

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