Ammonium Hydroxide → (E)-2-[2-(3-aminophenyl)ethenyl]-4-thiazolecarboxylic acid ethyl ester

HRID 327566Notes

Reaction equation

HRID 327566 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[S:9][CH:10]=1)=[O:5])[CH3:2].O.[Sn](Cl)Cl.[OH-].[NH4+]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 43835034Tin dichloride dihydrateHCID 67809803(E)-2-[2-(3-nitrophenyl)ethenyl]-4-thiazolecarboxylic acid ethyl ester

Product 1

HCID 14051204(E)-2-[2-(3-aminophenyl)ethenyl]-4-thiazolecarboxylic acid ethyl esterYield 81.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.5 g of (E)-2-[2-(3-nitrophenyl)ethenyl]-4-thiazolecarboxylic acid ethyl ester, 3.87 g of tin(II) chloride monohydrate and 100 ml of ethanol was heated to reflux for 16 hr. The reaction mixture was then poured onto ice-water, basified with ammonium hydroxide and extracted with methylene chloride. The methylene chloride solution was washed with water, saturated brine and dried (MgSO4). Evaporation of the solvent in vacuo yielded 1.1 g of (E)-2-[2-(3-aminophenyl)ethenyl]-4-thiazolecarboxylic acid ethyl ester; m.p. 112°-113° C. from ethanol.

Workup

  1. temperatureto reflux for 16 hr
  2. additionThe reaction mixture was then poured onto ice-water
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride solution was washed with water, saturated brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-adec0dee1f0d46039be5cbfded0ab2bd
Source dataset
uspto-grants-1993_12
Patent number
US05273986

Reaction notes

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