P-Anisidine → 4-Fluoro-1-[(4-methoxyphenyl)aminosulfonyl]-3-nitrobenzene

HRID 1595077Notes

Reaction equation

HRID 1595077 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]>CO>[F:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:19])=[O:18])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 27827994-Fluoro-3-nitrobenzene-1-sulfonyl chloride

Product 1

HCID 155506334-Fluoro-1-[(4-methoxyphenyl)aminosulfonyl]-3-nitrobenzeneYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

p-Anisidine (760 mg, 6.18 mmol) was added to a solution of 4-fluoro-3-nitrophenylsulfonyl chloride (740 mg, 3.09 mmol; Example A) in MeOH (10 ml) at ambient temperature. After stirring at room temperature for 15 min, the reaction mixture was concentrated under reduced pressure and the residue was taken up in ethyl acetate and filtered through a pad of silica gel. Concentration of the filtrate, followed by chromatography, provided 603 mg (60% yield) of the title compound. 1H-NMR (CDCl3): δ 8.42 (1H, dd, J=2.3, 6.8 Hz), 7.88 (1H, ddd, J=2.4, 4.0, 8.8 Hz), 7.33 (1H, dd, J=8.8, 9.9 Hz), 6.98 (2H, m), 6.81 (2H, m), 6.45 (1H, s), 3.77 (3H, s). MS (EI): 326 (11, M+), 122 (100). Anal. Calcd. for C13H11FN2O5S: C, 47.85; H, 3.40; N, 8.59; S, 9.83. Found: C, 47.68; H, 3.44; N, 8.54; S, 9.88.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. filtrationfiltered through a pad of silica gel

Sources & evidence

ORD record
ord-06a36705eb88492a9b2341214f43f124
Source dataset
uspto-grants-2001_09
Patent number
US06284923B1

Reaction notes

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