HCID 17381182, compound → HCID 22911642, compound

HRID 1378430Notes

Reaction equation

HRID 1378430 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)(=[O:4])=[O:3].[H][H]>CCO.[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 17381182HCID 17381182, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22911642HCID 22911642, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of the product from Step 2 (0.374 g, 1.72 mmol) in 95% EtOH (90 ml) was treated with 0.5 g of 10% palladium-on-carbon catalyst and hydrogenated at atmospheric pressure. The reaction was stopped when the theoretical amount of hydrogen had been consumed. The mixture was filtered through celite and the solid was extracted with warm (2:1) MeOH--CH2 cl2. The combined extracts and filtrate were concentrated and the residue was crystallized from MeOH to give 0.107 g of the titled product, mp 199°-202° C.

Workup

  1. customhad been consumed
  2. filtrationThe mixture was filtered through celite
  3. extractionthe solid was extracted
  4. temperaturewith warm (2:1) MeOH--CH2 cl2
  5. concentrationThe combined extracts and filtrate were concentrated
  6. customthe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-2bc715eab3be4f5c9a323c568aa8d590
Source dataset
uspto-grants-1997_09
Patent number
US05668157

Reaction notes

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