Pyridine → N-(4-chloro-3-nitrophenyl)methanesulfonamide

HRID 1962299

Reaction equation

HRID 1962299 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][S:13](Cl)(=[O:15])=[O:14].N1C=CC=CC=1>C1COCC1.Cl>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:13]([CH3:12])(=[O:15])=[O:14])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 124774-Chloro-3-nitroanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 3755760N-(4-chloro-3-nitrophenyl)methanesulfonamideYield 92.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-3-nitroaniline (5.0 g, 29 mmol), methanesulfonyl chloride (2.37 mL, 30.4 mmol) and pyridine (5.9 mL, 72.4 mmol) in THF (100 mL) was stirred for 24 h. Poured in 1M HCl (500 mL). The resulting precipitate was filtered and air-dried to provide the title compound as a solid (6.7 g, 92%).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customair-dried

Sources & evidence

ORD record
ord-61cf93d8f73b4f88bedce21cb30599fb
Source dataset
uspto-grants-2013_04
Patent number
US08415351B2

Linked notes

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