Hydrochloric Acid → 2-(5-Aminopyrid-2-ylamino)-1,1-bis(phenylsulphonyl)ethene

HRID 1905645Notes

Reaction equation

HRID 1905645 reaction equation
[C:1]1([S:7]([C:10]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])=[CH:11][NH:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][N:14]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[H][H]>[Pd].CN(C)C=O>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][CH:11]=[C:10]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:8])=[O:9])=[N:14][CH:15]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 155913871,1-Bis(phenylsulphonyl)-2-(5-nitropyrid-2-ylamino)etheneHCID 178418361HCID 178418361, compound

Product 1

HCID 155913922-(5-Aminopyrid-2-ylamino)-1,1-bis(phenylsulphonyl)etheneYield 24%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,1-bis(phenylsulphonyl)-2-(5-nitropyrid-2-ylamino)ethene (2.23 g), concentrated hydrochloric acid (2 ml), palladium on charcoal catalyst (5% w/w; 1.5 g) and dimethylformamide (50 ml) was hydrogenated at 25° C. and atmospheric pressure until three molar equivalents of hydrogen had been taken up. After filtration to remove the catalyst, the dimethylformamide was removed under vacuum below 40° C. and the residue was treated with methanol (25 ml) and stirred for 30 minutes, and then allowed to stand for 24 hours. The resulting solid was then filtered off, dissolved in chloroform (25 ml), treated with anhydrous potassium carbonate (5 g), and stirred from 2 hours. The mixture was filtered, and the chloroform was removed in vacuo. The resulting residue was recrystallised from a mixture of acetonitrile and diethyl ether and dried thoroughly at 100° C./0.1 mmHg, to give 2-(5-aminopyrid-2-ylamino)-1,1-bis(phenylsulphonyl)ethene (0.5 g), m.p. 172°-174° C.

Workup

  1. customwas hydrogenated at 25° C.
  2. filtrationAfter filtration
  3. customto remove the catalyst
  4. customthe dimethylformamide was removed under vacuum below 40° C.
  5. additionthe residue was treated with methanol (25 ml)
  6. waitto stand for 24 hours
  7. filtrationThe resulting solid was then filtered off
  8. dissolutiondissolved in chloroform (25 ml)
  9. additiontreated with anhydrous potassium carbonate (5 g)
  10. stirringstirred from 2 hours
  11. filtrationThe mixture was filtered
  12. customthe chloroform was removed in vacuo
  13. customThe resulting residue was recrystallised from a mixture of acetonitrile and diethyl ether
  14. customdried thoroughly at 100° C./0.1 mmHg

Sources & evidence

ORD record
ord-acc048f1f5b74660a202c3ad2bac912c
Source dataset
uspto-grants-1987_03
Patent number
US04647569

Reaction notes

Loading…