Methanesulfonyl chloride → HCID 86679430, compound

HRID 1776477Notes

Reaction equation

HRID 1776477 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH2:8])[CH2:3][CH2:2]1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>N1C=CC=CC=1>[CH:1]1([CH2:4][O:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[NH:8][S:14]([CH3:13])(=[O:16])=[O:15])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 196269232-(Cyclopropylmethoxy)aniline

Product 1

HCID 86679430HCID 86679430, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-(cyclopropylmethoxy)aniline (1.03 g, 6.31 mmol) in pyridine (20 ml) was cooled to 0° C., and methanesulfonyl chloride (0.541 ml, 6.94 mmol) was added. The mixture was warmed to RT and stirred for 2 hours. The solvent was removed, and the crude was portioned between EtOAc and HCl 1N. The organic phase was washed with brine and dried over Na2SO4. The solvent was removed and the crude was purified by filtration on silica gel cartridge (petroleum ether:EtOAc=80:20) affording N-(2-(cyclopropylmethoxy)phenyl)methanesulfonamide (1.456 g, 6.03 mmol, 96% yield, MS/ESI+ 263.9 [MNa]+).

Workup

  1. customThe solvent was removed
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. filtrationthe crude was purified by filtration on silica gel cartridge (petroleum ether:EtOAc=80:20)

Sources & evidence

ORD record
ord-77fa96ab6cbb42be897c6d7004b76095
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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