Water → HCID 19775579, compound

HRID 1613238Notes

Reaction equation

HRID 1613238 reaction equation
[CH2:1]([C:4]1[N:5]=[C:6]([S:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[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].O>C(O)C.[Ni]>[CH2:1]([C:4]1[N:5]=[C:6]([S:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[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

5

Reactant 2

HCID 962WaterHCID 19775538HCID 19775538, compound

Product 1

HCID 19775579HCID 19775579, compoundYield 21.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

3 g of ethyl 4-[[4-propyl-5-(4-nitrobenzyl)thiazol-2-yl]mercapto]butyrate in 50 ml of ethanol 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 brown oil obtained is taken up with acidified water. The aqueous phase is extracted with chloroform, rendered basic with dilute sodium hydroxide and extracted with ether. The ether solution is dried and concentrated to give a yellow oil, which is purified on a silica column (eluent: 7/3 cyclohexane/ethyl acetate) to give 0.6 g of ethyl 4-[[4-propyl-5-(4-aminobenzyl)thiazol-2-yl]mercapto]butyrate in the form of a pink oil.

Workup

  1. filtrationAfter filtration of the catalyst and concentration of the filtrate
  2. customthe brown oil obtained
  3. extractionThe aqueous phase is extracted with chloroform
  4. extractionextracted with ether
  5. dry with materialThe ether solution is dried
  6. concentrationconcentrated
  7. customto give a yellow oil, which
  8. customis purified on a silica column (eluent: 7/3 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-45907f4e55564882a1e535bd9ca27cdb
Source dataset
uspto-grants-1993_03
Patent number
US05192781

Reaction notes

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