Hydrochloric Acid → chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

HRID 363289Notes

Reaction equation

HRID 363289 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][CH2:13][S:14](Cl)(=[O:16])=[O:15].Cl>N1C=CC=CC=1>[Cl:12][CH2:13][S:14]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 677684-Fluoro-3-nitroanilineHCID 77054(Chloromethyl)sulfonyl chloride

Product 1

HCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-fluoro-3-nitroaniline (23.4 g, 0.15 mol) in anhydrous pyridine (120 mL) was added dropwise a solution of chloromethylsulfonyl chloride (22.35 g, 0.15 mol) at 0° C. under a nitrogen atmosphere. The mixture was then stirred at 0°-5° C. for 4 h and then the mixture was poured onto ice (1500 g) containing concentrated aqueous hydrochloric acid (300 mL). The mixture was filtered, and the residue was dissolved in methylene chloride (1200 mL). After drying (MgSO4) and concentration under reduced pressure, the crude product was dissolved in 1-chlorobutane:ether 9:1 v/v and passed through silica gel. The eluent was concentrated under reduced pressure to give the title compound of Step A.

Workup

  1. additionthe mixture was poured onto ice (1500 g)
  2. filtrationThe mixture was filtered
  3. dissolutionthe residue was dissolved in methylene chloride (1200 mL)
  4. customAfter drying
  5. concentration(MgSO4) and concentration under reduced pressure
  6. dissolutionthe crude product was dissolved in 1-chlorobutane:ether 9:1 v/v
  7. concentrationThe eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8fb31bb7dc764c4d8ff9f7380c1155b9
Source dataset
uspto-grants-1999_02
Patent number
US05874382

Reaction notes

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