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

HRID 1930260

Reaction equation

HRID 1930260 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-828c0e7b494849c1a446e7d8277280bf
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Linked notes

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