HCID 24838528, compound → HCID 24838477, compound

HRID 1613241Notes

Reaction equation

HRID 1613241 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]([NH:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[S:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=1)[CH2:2][CH3:3]>CO.[Ni]>[CH2:1]([C:4]1[N:5]=[C:6]([NH:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])[S:7][C:8]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 24838528HCID 24838528, compound

Product 1

HCID 24838477HCID 24838477, compoundYield 75.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2.6 g of methyl (4-propyl-5-(4-nitrobenzyl)thiazol-2-yl)aminoacetate in 60 ml of methanol are hydrogenated at normal pressure and room temperature in the presence of Raney nickel. After filtration of the catalyst and concentration of the filtrate, the residue is taken up with acidified water. The aqueous phase is extracted with ether, rendered basic with sodium carbonate and extracted with ethyl acetate. After drying and concentration, the residue is taken up with pentane to give 1.8 g of methyl (4-propyl-5-(4-aminobenzyl)thiazol-2-yl)aminoacetate in the form of a beige solid melting at 106° C.

Workup

  1. filtrationAfter filtration of the catalyst and concentration of the filtrate
  2. extractionThe aqueous phase is extracted with ether
  3. extractionextracted with ethyl acetate
  4. customAfter drying
  5. concentrationconcentration

Sources & evidence

ORD record
ord-eff8ea95f57f4870bc9ce38f1625399d
Source dataset
uspto-grants-1993_03
Patent number
US05192781

Reaction notes

Loading…