Pyridine → N-[4-(3-chloro-1-propylthio)phenyl]methanesulfonamide

HRID 1030280Notes

Reaction equation

HRID 1030280 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][S: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][S: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 149330561-Chloro-3-(4-aminothiophenoxy)propane

Product 1

HCID 19822356N-[4-(3-chloro-1-propylthio)phenyl]methanesulfonamideYield 59.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooded (5° C.) solution of 1-chloro-3-(4-aminothiophenoxy)propane (4.9 g, 0.024 mol) and pyridine (2.1 g 0.027 mol) in CH2Cl2 (50 mL) was added methanesulfonyl chloride (3.1 g, 0.027 mol). The mixture was stirred at room temperature for 16 hours, washed with 2 N HCl, brine, dried (MgSO4), and concentrated. Recrystallization from EtOH gave 4.0 g (59%) of product as a pink solid m.p. 61°-63° C.

Workup

  1. washwashed with 2 N HCl, brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customRecrystallization from EtOH

Sources & evidence

ORD record
ord-4bc1a13eb0c9424cab30c87e31942de7
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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