Sodium Hydroxide → 4-Isopropyl-2-(trans-3-aminostyryl) thiazole

HRID 1199699Notes

Reaction equation

HRID 1199699 reaction equation
[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[CH:1]([C:4]1[N:5]=[C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([NH2:17])[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 157183584-Isopropyl-2-(trans-3-nitrostyryl)thiazole

Product 1

HCID 140511654-Isopropyl-2-(trans-3-aminostyryl) thiazoleYield 47.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 16.8 g of 4-isopropyl-2-(trans-3-nitrostyryl)thiazole dissolved in 60 ml of ethanol was added a solution of 48.4 g of stannous chloride dihydrate in 60 ml of ethanol and the mixture was refluxed for 1.5 hours. After the reaction mixture was cooled to room temperature, the mixture was adjusted to pH 13 with addition of 30% aqueous sodium hydroxide solution and then the basic portion was extracted with the use of ethyl acetate and dried over magnesium sulfate, followed by evaporation of the solvent under reduced pressure. The solid residue formed was recrystallized from ethyl ether-n-hexane to obtain 7.1 g (yield 47%) of the pale yellowish white title compound.

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. extractionthe basic portion was extracted with the use of ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. customfollowed by evaporation of the solvent under reduced pressure
  5. customThe solid residue formed
  6. customwas recrystallized from ethyl ether-n-hexane

Sources & evidence

ORD record
ord-509d11c8326f49169fd29aa77441b979
Source dataset
uspto-grants-1990_02
Patent number
US04902700

Reaction notes

Loading…