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

HRID 1930259Notes

Reaction equation

HRID 1930259 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-0f7b3e0ab8a649e39227c695d8598155
Source dataset
uspto-grants-2012_05
Patent number
US08188104B2

Reaction notes

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