2-Dimethylaminopyridine → chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamide

HRID 1934847Notes

Reaction equation

HRID 1934847 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].CN(C1C=CC=CN=1)C>ClCCl.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

6

Reactant 3

HCID 218852-DimethylaminopyridineHCID 677684-Fluoro-3-nitroanilineHCID 77054(Chloromethyl)sulfonyl chloride

Product 1

HCID 18760842chloro-N-(4-fluoro-3-nitrophenyl)methanesulfonamideYield 93.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

20 g of 4-fluoro-3-nitroaniline (128 mmol) was dissolved in a mixture of 200 mL of dichloromethane and 40 mL of pyridine. To this solution was added 21 g (140 mmol) of chloromethylsulfonyl chloride dropwise at 20-30° C., followed by the addition of 3.21 g of dimethylaminopyridine. The solution was stirred for an additional 3 hours. The reaction mixture was transferred into a separatory funnel and washed sequentially with water (twice with 25 mL), 5% HCl (twice with 25 mL), and water (25 mL). The organic phase was separated, dried (MgSO4), filtered and concentrated under reduced pressure to yield 32 g (93%) of the title compound as a solid melting at 112-113° C.

Workup

  1. customThe reaction mixture was transferred into a separatory funnel
  2. washwashed sequentially with water (twice with 25 mL), 5% HCl (twice with 25 mL), and water (25 mL)
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92bdf0a3b9544e6f980b1601b62aca34
Source dataset
uspto-grants-2002_05
Patent number
US06384234B1

Reaction notes

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