Pyridine → 4-bromo-N-methylbenzene-1-sulfonamide

HRID 54983

Reaktionsgleichung

Reaktionsgleichung von HRID 54983
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N:12]1C=CC=C[CH:13]=1.CN>C(Cl)Cl>[CH3:13][NH:12][S:8]([C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 6329MethylamineHCID 7396p-Bromobenzenesulfonyl chloride

Produkt 1

HCID 1012154-bromo-N-methylbenzene-1-sulfonamideAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 4-bromophenylsulfonyl chloride (25.5 g, 100 mmol), CH2Cl2 (400 mL) and pyridine (1.6 g, 110 mol) was cooled to 0° C. and methylamine gas was added over 45 minutes. The mixture was warmed to room temperature, the solvent was removed in vacuo and the residue was dissolved in CH2Cl2 and washed with 2N HCl (2×100 mL), water (1×200 mL), saturated NaHCO3 (1×200 mL) and then brine (1×200 mL). The solvent was dried over MgSO4 and the solvent was removed in vacuo to afford 23 g of N-methyl-4-bromophenylsulfonamide.

Aufarbeitung

  1. temperatureThe mixture was warmed to room temperature
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in CH2Cl2
  4. washwashed with 2N HCl (2×100 mL), water (1×200 mL), saturated NaHCO3 (1×200 mL)
  5. dry with materialThe solvent was dried over MgSO4
  6. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3a409d6324b644c8af5081f4794056a9
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624922

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