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Triethylamine → N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide

HRID 541829
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HRID 541829 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([Cl:31])=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+].C(N(CC)CC)C>CN(C=O)C>[Cl:23][C:24]1[N:29]=[C:28]([NH:1][C:2]2[CH:3]=[C:4]([NH:8][S:9]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=2)[C:27]([Cl:31])=[CH:26][N:25]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 66881065N-(3-Aminophenyl)-1-(3-nitrophenyl)methanesulfonamide Hydrochloride

생성물 1

HCID 86636268N-{3-[(2,5-Dichloropyrimidin-4-yl)amino]phenyl}-1-(3-nitrophenyl)methanesulfonamide수율 60.7%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

To a solution of N-(3-aminophenyl)-1-(3-nitrophenyl)methanesulfonamide-hydrogen chloride (0.10 g, 0.29 mmol) and 2,4,5-trichloropyrimidine (0.065 g, 0.35 mmol) in DMF (1 mL) was added potassium carbonate (0.20 g, 1.4 mmol). The resulting mixture was stirred overnight at room temperature. Additional triethylamine (0.099 mL, 0.71 mmol) was added and stirred again overnight. The reaction was then quenched with sat'd NH4Cl and water. EtOAc was added and the layers separated. The aqueous phase was extracted with EtOAc. The combined organics were washed with water and brine then dried (MgSO4), filtered, and concentrated. The crude was purified by column chromatography to give the desired product (0.080 g, 60%). LCMS for C17H13Cl2N5O4S (M+H)+: m/z=453.9, 455.9.

후처리

  1. stirringstirred again overnight
  2. customThe reaction was then quenched with sat'd NH4Cl and water
  3. additionEtOAc was added
  4. customthe layers separated
  5. extractionThe aqueous phase was extracted with EtOAc
  6. washThe combined organics were washed with water and brine
  7. dry with materialthen dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude was purified by column chromatography

출처 및 근거

ORD 기록
ord-0b20f03c7f0c4902ba47c684a3307e39
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08871753B2

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