ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate → ethyl N-(4-p-aminophenyl-2-thiazolyl)carbamate

HRID 1980825Notes

Reaction equation

HRID 1980825 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:20])[O:17][CH2:18][CH3:19])[S:13][CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:20])[O:17][CH2:18][CH3:19])[S:13][CH:14]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 5108134ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 15916633ethyl N-(4-p-aminophenyl-2-thiazolyl)carbamateYield 72.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In 500 ml of ethyl acetate, was dissolved 4 g of ethyl N-(4-p-nitrophenyl-2-thiazolyl)carbamate, followed by an addition of 3 g of a 10% palladium/carbon catalyst. The mixture was then subjected under normal pressure to reduction with hydrogen gas. The catalyst was filtered off. The filtrate was concentrated and subjected to column chromatography on silica gel. The reaction product was eluted with a chloroform/ethylacetate mixed solvent. The resulting product was then recrystallized from methanol to obtain 2.6 g of ethyl N-(4-p-aminophenyl-2-thiazolyl)carbamate.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationThe filtrate was concentrated
  3. washThe reaction product was eluted with a chloroform/ethylacetate mixed solvent
  4. customThe resulting product was then recrystallized from methanol

Sources & evidence

ORD record
ord-a8636db37ef64995bc39fcef3690ec6f
Source dataset
uspto-grants-1985_04
Patent number
US04511574

Reaction notes

Loading…