Hydrochloric Acid → Benzenesulfonamide, N-(4-nitrophenyl)-

HRID 1393828Notes

Reaction equation

HRID 1393828 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>N1C=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][S:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:19])=[O:18])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 74754-Nitroaniline

Product 1

HCID 231837Benzenesulfonamide, N-(4-nitrophenyl)-Yield 99.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of p-nitroaniline (1 kg, 7.245 mol) in pyridine (3.6 L) was brought to 45° C. Benzenesulfonyl chloride (1.41 kg, 8 mol) was poured in over 70 minutes, while maintaining the temperature ranging from 45 to 50° C. After 1 hour at 50° C., the reaction medium was poured onto 8 kg of ice and 4.35 L of hydrochloric acid. A yellow precipitate formed and was filtered off by suction and then dissolved in 20 L of 0.5 N sodium hydroxide at 55° C. The insoluble matter was removed by filtration and the filtrate was then neutralized hydrochloric acid while still hot. A yellow precipitate formed and was filtered off by suction, reslurried in water, and then air-dried. 2 kg of product with a melting point of 137° C. were obtained.

Workup

  1. customwas brought to 45° C
  2. temperaturewhile maintaining the temperature
  3. customranging from 45 to 50° C
  4. customA yellow precipitate formed
  5. filtrationwas filtered off by suction
  6. dissolutiondissolved in 20 L of 0.5 N sodium hydroxide at 55° C
  7. customThe insoluble matter was removed by filtration
  8. customA yellow precipitate formed
  9. filtrationwas filtered off by suction
  10. customair-dried

Sources & evidence

ORD record
ord-5fd1610f50784498ac1c4ad209b9d9c3
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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