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

HRID 2360006Notes

Reaction equation

HRID 2360006 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10])[NH2:5].[CH3:12][S:13](Cl)(=[O:15])=[O:14].N1C=CC=CC=1>C1COCC1.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][S:13]([CH3:12])(=[O:15])=[O:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 699963-Chloro-4-nitroaniline

Product 1

HCID 12254687N-(3-chloro-4-nitrophenyl)methanesulfonamideYield 100%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-chloro-4-nitroaniline (4.85 g, 28.1 mmol), methanesulfonyl chloride (3.29 mL, 42.2 mmol) and pyridine (6.82 mL, 84 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 (7.03 g, 100%).

Workup

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

Sources & evidence

ORD record
ord-36ffc9d3135149df8c0cb4a000c8314d
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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