Methylamine → 4-(Bromomethyl)-N-methylbenzenesulfonamide

HRID 2041110

Reaktionsgleichung

Reaktionsgleichung von HRID 2041110
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][NH2:20]>C1COCC1>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:20][CH3:19])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Produkt 1

HCID 100156454-(Bromomethyl)-N-methylbenzenesulfonamideAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Mix 4-(bromomethyl)benzenesulfonyl chloride (2.7 g, 10 mmol), anhydrous potassium carbonate (1.4 g, 10 mmol) and anhydrous THF (60 mL) under nitrogen. Cool the mixture in an ice bath, add dropwise a 2M solution of methylamine in THF, and stir at this temperature for 30 min. Remove the ice bath and stir at ambient temperature for 16 h. Dilute with EtOAc then wash with 1N aqueous HCl. Separate the organic layer, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7) to obtain the title compound (1.5 g, 71%). MS (ES+) m/z: 266 (M+H)+.

Aufarbeitung

  1. temperatureCool the mixture in an ice bath
  2. customRemove the ice bath
  3. stirringstir at ambient temperature for 16 h
  4. additionDilute with EtOAc
  5. washthen wash with 1N aqueous HCl
  6. customSeparate the organic layer
  7. dry with materialdry over Na2SO4
  8. concentrationconcentrate in vacuo
  9. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 4:1, 7:3 and 13:7)

Quellen und Nachweise

ORD-Eintrag
ord-9c3706d5bf73455f8f178b2559803b28
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08580780B2

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