Hydrochloric Acid → N-(m-Nitrophenyl)benzenesulphonamide

HRID 2044090Notes

Reaction equation

HRID 2044090 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17])([O-:13])=[O:12].Cl>N1C=CC=CC=1>[N+:11]([C:14]1[CH:15]=[C:16]([NH:17][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])[CH:18]=[CH:19][CH:20]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 74233-Nitroaniline

Product 1

HCID 66459N-(m-Nitrophenyl)benzenesulphonamideYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Benzenesulfonyl chloride (6.01 mL, 46.8 mmol) was added to a solution of 3-nitroaniline (6.47 g, 46.8 mmol) in pyridine (50 mL) at room temperature. The mixture was heated to 100° C. for 1 h. Most of the pyridine was evaporated under reduced pressure. The resulting brown oil was dissolved in CH2Cl2 (100 mL) and washed with aqueous HCl (150 mL, 50 mmol). A tan solid precipitated out from the acidic aqueous phase. The solid was collected by filtration, washed with CH2Cl2 and dried under vacuum (10.41 g, 80% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.95 (1H, s), 7.93 (1H, s), 7.85-7.89 (1H, m), 7.79-7.83 (2H, m), 7.61-7.67 (1H, m), 7.49-7.61 (4H, m).

Workup

  1. customMost of the pyridine was evaporated under reduced pressure
  2. dissolutionThe resulting brown oil was dissolved in CH2Cl2 (100 mL)
  3. customA tan solid precipitated out from the acidic aqueous phase
  4. filtrationThe solid was collected by filtration
  5. washwashed with CH2Cl2
  6. customdried under vacuum (10.41 g, 80% yield)

Sources & evidence

ORD record
ord-fb6583eca97749ccbf83ae0765ee2e25
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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