Water → HCID 24838476, compound

HRID 1613233Notes

Reaction equation

HRID 1613233 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[S:5][C:6]=1[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1.O>C(O)C.COC(O)C.[Ni]>[CH3:1][C:2]1[N:3]=[C:4]([NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[S:5][C:6]=1[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 962WaterHCID 24838526HCID 24838526, compound

Product 1

HCID 24838476HCID 24838476, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 86746606HCID 86746606, compoundSolvent

Procedure

9.2 g of ethyl (4-methyl-5-(4-nitrobenzyl)thiazol-2-yl)aminoacetate in 500 ml of an ethanol/methoxyethanol mixture are hydrogenated at normal pressure and room temperature in the presence of Raney nickel. After filtration of the catalyst and concentration of the reaction medium, a brown oil is obtained which is taken up with acidified water, the aqueous phase is extracted with chloroform and then rendered basic and the precipitate obtained is filtered off to give 6.1 g of ethyl (4-methyl-5-(4-aminobenzyl)thiazol-2-yl)aminoacetate in the form of a brown solid melting at 116° C.

Workup

  1. filtrationAfter filtration of the catalyst and concentration of the reaction medium
  2. customa brown oil is obtained which
  3. extractionthe aqueous phase is extracted with chloroform
  4. customthe precipitate obtained
  5. filtrationis filtered off

Sources & evidence

ORD record
ord-eb96a2b7badf488ea8325a712b7613eb
Source dataset
uspto-grants-1993_03
Patent number
US05192781

Reaction notes

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