HCID 13280056, compound → HCID 13280058, compound

HRID 2164788Notes

Reaction equation

HRID 2164788 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=2[C:16]([NH:18][CH2:19][CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[O:17])(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH:13][C:14]2[CH:30]=[CH:29][CH:28]=[CH:27][C:15]=2[C:16]([NH:18][CH2:19][CH2:20][CH2:21][N:22]2[CH:26]=[CH:25][N:24]=[CH:23]2)=[O:17])(=[O:12])=[O:11])=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 13280056HCID 13280056, compound

Product 1

HCID 13280058HCID 13280058, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-(4-Nitrobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide (38.4 g) was dissolved in glacial acetic acid (30 ml) and 5% w/w palladium-on-charcoal (8.0 g) was added. The mixture was stirred under an atmosphere of hydrogen for 4 hours, filtered free of catalyst and evaporated. The solid residue was dissolved in water and the solution was adjusted to pH 9 by the addition of aqueous ammonia. The solid which had precipitated was collected and recrystallised from ethanol to give 2-(4-aminobenzenesulphonamido)-N-(3-imidazol-1-ylpropyl)benzamide (26.7 g) in the form of a white solid, m.p. 171°-175° C.

Workup

  1. filtrationfiltered free of catalyst
  2. customevaporated
  3. dissolutionThe solid residue was dissolved in water
  4. additionthe solution was adjusted to pH 9 by the addition of aqueous ammonia
  5. customThe solid which had precipitated
  6. customwas collected
  7. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-f9c1e095f44844fcab9c7cd66bdae46d
Source dataset
uspto-grants-1985_03
Patent number
US04507315

Reaction notes

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