Pyridine → HCID 1237829, compound

HRID 1048979Notes

Reaction equation

HRID 1048979 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].N1C=CC=CC=1.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>C(Cl)Cl>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:19]([CH3:18])(=[O:21])=[O:20])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 1237829HCID 1237829, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-fluoro-3-nitroaniline (0.5 g, 0.023 mol) in DCM (10 ml) and pyridine (0.98 g, 0.012 mol) was added methanesulfonyl chloride (0.54 g, 0.0048 mol) portion wise at 0° C. with constant stirring. The reaction mixture was allowed to stir at 0° C. for 4 h. The reaction mixture was concentrated and diluted with water (20 ml) and extracted with DCM (3×15 ml). The combined organic layers were washed with 1 N HCl and NaHCO3 solution dried over Na2SO4 and concentrated in vacuo to afford the desired product N-(4-fluoro-3-nitrophenyl)methane sulfonamide as off a white solid. 1H NMR (400 MHz, DMSO-d6), δ: 10.23 (s, 1H), 7.93-7.91 (d, J=8.4 Hz, 1H), 7.62-7.54 (m, 2H), 3.59 (s, 3H). LCMS (ES) m/e MS (M−1=233). Purity: 80%.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water (20 ml)
  3. extractionextracted with DCM (3×15 ml)
  4. washThe combined organic layers were washed with 1 N HCl and NaHCO3 solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ec2870b0254247c3a11fe266d47ad439
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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