Methylamine → 4-(Bromomethyl)-N-methylbenzenesulfonamide

HRID 911220Notes

Reaction equation

HRID 911220 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-b9e8bcc7cb6a40af87ab009292abfafe
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

Loading…