Reaction #2006462

Reaction equation

ethyl acetate

sodium hydride

2,5-dimethyl-4-hydroxyaniline

3-(tert-butyl)-5-chloro-1,2,4-thiadiazole

→

4-[(3-(tert-Butyl)-1,2,4-thiadiazol-5-yl)oxy]-2,5-dimethylaniline

Yield 90.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   workup.ADDITIONare added
2. 2
   Temperaturecooled down to AT
3. 3
   Extractionthe solution is extracted three times with water
4. 4
   Dryingdried over MgSO4
5. 5
   Otherthe solvent is removed under vacuum (1.46 g, 94% purity, 90% yield, log P (pH 2.3)=3.29)

Procedure

754 mg (5.50 mmol) of 2,5-dimethyl-4-hydroxyaniline are dissolved in 5 ml of N,N-dimethylformamide and slowly treated with 242 mg (6.05 mmol) of sodium hydride. The reaction mixture is stirred for 15 min, before 972 mg (5.50 mmol) of 3-(tert-butyl)-5-chloro-1,2,4-thiadiazole are added. Subsequently, the reaction mixture is heated at 100° C. for 1 h and then cooled down to AT. After addition of 20 ml of ethyl acetate, the solution is extracted three times with water and dried over MgSO4, and the solvent is removed under vacuum (1.46 g, 94% purity, 90% yield, log P (pH 2.3)=3.29).

Source