Water → 2-Methoxymethyl-4-propyl-5-(4-aminobenzyl)thiazole

HRID 1613240Notes

Reaction equation

HRID 1613240 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=2)=[C:7]([CH2:9][CH2:10][CH3:11])[N:8]=1.O>CO.[Ni]>[CH3:1][O:2][CH2:3][C:4]1[S:5][C:6]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([NH2:19])=[CH:17][CH:18]=2)=[C:7]([CH2:9][CH2:10][CH3:11])[N:8]=1

Participants

5

Reactant 2

HCID 962WaterHCID 19775540HCID 19775540, compound

Product 1

HCID 197755572-Methoxymethyl-4-propyl-5-(4-aminobenzyl)thiazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

0.9 of 2-methoxymethyl-4-propyl-5-(4-nitrobenzyl)thiazole in 50 ml of methanol is hydrogenated at normal pressure and room temperature in the presence of Raney nickel. After filtration of the catalyst and concentration of the filtrate, the brown oil obtained is taken up with acidified water. The aqueous phase is extracted with ether, rendered basic with dilute sodium hydroxide and extracted with ethyl acetate. The organic phase is dried and concentrated to give 0.5 g of 2-methoxymethyl-4-propyl-5-(4-aminobenzyl)thiazole in the form of an orange oil, which is used as such for the next step.

Workup

  1. filtrationAfter filtration of the catalyst and concentration of the filtrate
  2. customthe brown oil obtained
  3. extractionThe aqueous phase is extracted with ether
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-291153c75bb64ab7a281eea7dc8a7e34
Source dataset
uspto-grants-1993_03
Patent number
US05192781

Reaction notes

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