Pyridine → N-[4-(3-Chloro-1-propyloxy)phenyl]methanesulfonamide

HRID 1030275Notes

Reaction equation

HRID 1030275 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 198223581-Chloro-3-(4-aminophenoxy)propane

Product 1

HCID 19822347N-[4-(3-Chloro-1-propyloxy)phenyl]methanesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 1-chloro-3-(4-aminophenoxy)propane (680 mg, 3.66 mmol) and pyridine (319 mg, 4.03 mmol) in CH2Cl2 (10 mL) was added methanesulfonyl chloride (461 mg, 4.03 mmol). After 18 hours, the mixture was washed with 1N HCl and brine, dried (MgSO4), and concentrated to give 865 mg (90%) of product as an off-white solid m.p. 120°-122° C.

Workup

  1. washthe mixture was washed with 1N HCl and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0a35b9fe20ce4f99988870b8852a2946
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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