4-Nitrobenzenesulfonyl chloride → HCID 27301538, compound

HRID 1754115Notes

Reaction equation

HRID 1754115 reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6].[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([O-:15])=[O:14]>N1C=CC=CC=1>[N+:13]([C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[O:3][C:2]([F:11])([F:12])[F:1])(=[O:24])=[O:23])=[CH:20][CH:21]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 737542-(Trifluoromethoxy)aniline

Product 1

HCID 27301538HCID 27301538, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
85 °C

Procedure

To a pre-cooled solution of 2-(trifluoromethoxy)aniline (1.8 g, 10.16 mmol) in pyridine (20 ml) was added 4-nitrobenzene-1-sulfonyl chloride (2.252 g, 10.16 mmol) in 5-10 mL of pyridine at 0° C. slowly. The reaction mixture was stirred and heated to 85° C. for 3 h, then cooled down to 45° C. and stirred at the same temperature over weekend. The solvent was removed under reduced pressure. The residue was diluted with methylene chloride and washed with 1N HCl (×2), water (×2), and brine. The organic layer was separated, dried with anhydrous Na2SO4, filtered and concentrated under reduced pressure to give 2.82 g of title product.

Workup

  1. temperaturecooled down to 45° C.
  2. stirringstirred at the same temperature over weekend
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was diluted with methylene chloride
  5. washwashed with 1N HCl (×2), water (×2), and brine
  6. customThe organic layer was separated
  7. dry with materialdried with anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d27b79954944e76b47e122f20afdc49
Source dataset
uspto-grants-2015_10
Patent number
US09169209B2

Reaction notes

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