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Hydrochloric Acid → N-(4-fluoro-3-nitrophenyl)benzenesulfonamide

HRID 840094
Notes
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Reaction equation

HRID 840094 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].[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.Cl>N1C=CC=CC=1>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][S:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:20])=[O:19])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 677684-Fluoro-3-nitroaniline

Product 1

HCID 4599069N-(4-fluoro-3-nitrophenyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

4-fluoro-3-nitro-aniline (7.8 g, 50 mmol) is taken up in 50 mL pyridine and cooled to 10° C. The benzenesulphonic acid chloride (7.0 mL, about 55 mmol) is added dropwise with stirring within about 20 min at 10-20° C. The mixture is stirred for about 0.5 h at ambient temperature and poured onto ice water. After acidifying with conc. hydrochloric acid the mixture is extracted with 150 mL ethyl acetate, washed with water, dried and concentrated by evaporation. The residue is dissolved in diethylether, diluted with petroleum ether and cooled. The crystals formed are filtered off, washed with diethylether/petroleum ether and dried.

Workup

  1. stirringThe mixture is stirred for about 0.5 h at ambient temperature
  2. additionpoured onto ice water
  3. extractionis extracted with 150 mL ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated by evaporation
  7. dissolutionThe residue is dissolved in diethylether
  8. additiondiluted with petroleum ether
  9. temperaturecooled
  10. customThe crystals formed
  11. filtrationare filtered off
  12. washwashed with diethylether/petroleum ether
  13. customdried

Sources & evidence

ORD record
ord-650ab8ffa741407f9a92a82023744ad0
Source dataset
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06365584B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes