N-(3-aminophenyl)benzenesulfonamide → HCID 178467267, compound

HRID 2398715Notes

Reaction equation

HRID 2398715 reaction equation
[H][H].[C:3]1([S:9]([NH:12][C:13]2[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=2)[NH2:16])(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:20]([C:23]1[C:24](=[O:34])[O:25][C:26]([OH:33])=[C:27]([C:30](=O)[CH3:31])[C:28]=1[OH:29])(=[O:22])[CH3:21]>[Pd].C(O)C>[C:20]([C:23]1[C:24](=[O:34])[O:25][C:26](=[O:33])[C:27](=[C:30]([NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:13]([NH:12][S:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)(=[O:10])=[O:11])[CH:14]=2)[CH3:31])[C:28]=1[OH:29])(=[O:22])[CH3:21]

Participants

6

Reactant 3

HCID 11849198N-(3-aminophenyl)benzenesulfonamideHCID 1354659693,5-Diacetyl-2,6-dihydroxy-4h-pyran-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 178467267HCID 178467267, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

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. dissolution(0.005 mol), is dissolved in 100 ml
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is used directly in the subsequent reaction
  4. additionThus the ethanolic solution (100 ml.) containing 1.2 g
  5. concentrationThe reaction mixture is concentrated
  6. filtrationfiltered

Sources & evidence

ORD record
ord-7f1467d2686c4a3cacc228c1fd814fb5
Source dataset
uspto-grants-1977_05
Patent number
US04025614

Reaction notes

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