2,6-Lutidine → N-[3-(Chloromethyl)phenyl]methanesulfonamide

HRID 1162196Notes

Reaction equation

HRID 1162196 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[CH:6][CH:7]=1.[Cl-:10].[Li+].N1C(C)=CC=CC=1C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>CN(C=O)C.O>[Cl:10][CH2:8][C:4]1[CH:3]=[C:2]([NH:1][S:21]([CH3:20])(=[O:23])=[O:22])[CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 79372,6-LutidineHCID 31297Methanesulfonyl chlorideHCID 802933-Aminobenzyl alcoholHCID 433294Lithium Chloride

Product 1

HCID 11053164N-[3-(Chloromethyl)phenyl]methanesulfonamideYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (3-amino-phenyl)-methanol (388 mg, 3.15 mmoles), lithium chloride (270 mg, 6.3 mmoles) and 2,6-lutidine (0.821 mL, 6.93 mmoles) in DMF (10 mL) was cooled at 0° C. under nitrogen atmosphere. Methanesulphonylchloride (0.536 mL, 6.93 mmoles) was added dropwise, and the mixture was stirred at room temperature for 3 hours. Water (30 mL) was then added, and the mixture was extracted with AcOEt (3×40 mL). The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness. The crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 10/0 to 8/2) to yield 330 mg of the title compound.

Workup

  1. extractionthe mixture was extracted with AcOEt (3×40 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness
  5. customThe crude material was purified by flash chromatography (SiO2, petroleum ether/AcOEt from 10/0 to 8/2)

Sources & evidence

ORD record
ord-9a4231ae9d064854b9f91e1d4b7f945e
Source dataset
uspto-grants-2010_10
Patent number
US07820698B2

Reaction notes

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