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

HRID 1936198Notes

Reaction equation

HRID 1936198 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 stining 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-1a793013bf3144bbb0c0e8a6ff0b4c24
Source dataset
uspto-grants-2002_05
Patent number
US06388131B2

Reaction notes

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