HCID 19735472, compound → HCID 19735358, compound

HRID 326717Notes

Reaction equation

HRID 326717 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:17]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)=[C:16]([O:27][CH2:28][CH2:29][OH:30])[N:15]=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)(=O)C.Cl.O1CCOCC1.[C].[Pd]>[ClH:1].[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]2[C:12]([NH:11][S:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)(=[O:10])=[O:9])=[N:13][CH:14]=[N:15][C:16]=2[O:27][CH2:28][CH2:29][OH:30])=[CH:19][CH:20]=1

Participants

6

Reactant 1

HCID 19735472HCID 19735472, compound

Product 1

HCID 19735358HCID 19735358, compound

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

200 mg of p-chloro-N-[6-(2-hydroxyethoxy)-5-(p-nitrophenyl)-4-pyrimidinyl]benzenesulfonamide in 15 ml of glacial acetic acid and 2 ml of 4N HCl in dioxane were hydrogenated over 50 mg of palladium-carbon (10%) at room temperature and normal pressure. After filtering the catalyst under suction, the solution was evaporated under reduced pressure. The residue was dissolved in 30 ml of methanol and the solution was treated with 1 ml of dioxane-HCl. After 16 hours, the solution was evaporated under reduced pressure and the residue was recrystallized from methanol and acetonitrile. There was obtained N-[5-(p-aminophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-p-chlorobenzenesulfonamide hydrochloride, melting point 206° C. (with decompositon).

Workup

  1. filtrationAfter filtering the catalyst under suction
  2. customthe solution was evaporated under reduced pressure
  3. dissolutionThe residue was dissolved in 30 ml of methanol
  4. additionthe solution was treated with 1 ml of dioxane-HCl
  5. customthe solution was evaporated under reduced pressure
  6. customthe residue was recrystallized from methanol and acetonitrile

Sources & evidence

ORD record
ord-a862ae655e6b4d0781b2cae3e24c8dd9
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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