Hydrochloric Acid → N-(m-Nitrophenyl)benzenesulphonamide

HRID 2398714Notes

Reaction equation

HRID 2398714 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([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>[C:11]1([S:17]([NH:7][C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][CH:8]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 74233-Nitroaniline

Product 1

HCID 66459N-(m-Nitrophenyl)benzenesulphonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.76 g. (0.02 mol) of m-nitroaniline in 5 ml. of pyridine cooled to 0° C. is added 3.52 g. (0.02 mol) of benzenesulfonyl chloride dropwise and the mixture is stirred for one hour at room temperature. The reaction mixture is decomposed with dilute hydrochloric acid and ice, and the solid filtered off to give m-(phenylsulfonamido)-nitrobenzene, m.p. 132°-134° C. The latter, 1.4 g. (0.005 mol), is dissolved in 100 ml. of ethanol, 300 mg. of 10% palladium-on-carbon is added and the mixture is hydrogenated in a Parr shaker. After hydrogen uptake has ceased, the catalyst is filtered off and the filtrate is used directly in the subsequent reaction. Thus the ethanolic solution (100 ml.) containing 1.2 g. (0.005 mol) of 3-phenylsulfonamidoaniline and 1.06 g. (0.005 mol) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one is refluxed for one hour. The reaction mixture is concentrated and filtered to give 5-acetyl-4-hydroxy-3 -[1-(3-phenylsulfonamidophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. 209° C.

Workup

  1. additionis added 3.52 g
  2. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-1bbdcbf94d0548ca831708a085bbff20
Source dataset
uspto-grants-1977_05
Patent number
US04025614

Reaction notes

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