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

HRID 508320

Reaction equation

HRID 508320 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-f5302eb0b8d446168e6a8241f2a5a7dc
Source dataset
uspto-grants-2015_08
Patent number
US09095590B2

Linked notes

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