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

HRID 508319Notes

Reaction equation

HRID 508319 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-db600a64b1fa4132b6b53e91afa40186
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Reaction notes

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