Reaction #2006461

Reaction equation

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

trimethyl orthoformate

N-ethyl-N-methylamine

→

N′-{4-[(3-(tert-butyl)-1,2,4-thiadiazol-5-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide

Yield 59.0%

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux for 2 h
3. 3
   Otherthe solvent is evaporated under vacuum
4. 4
   OtherAfter removing the solvent
5. 5
   Otherthe crude product is purified by column chromatography (13.4 g, 59% yield, 95% purity, log P (pH 2.3)=2.02)

Procedure

17.46 g (63.00 mmol) of 4-[(3-(tert-butyl)-1,2,4-thiadiazol-5-yl)oxy]-2,5-dimethylaniline are dissolved in 500 ml of trimethyl orthoformate and heated at reflux for 2 h. After cooling to ambient temperature (AT), the solvent is evaporated under vacuum and the residue is taken up in 630 ml of dichloromethane, treated with 8.65 ml (126.00 mmol) of N-ethyl-N-methylamine and stirred at ambient temperature for 18 h. After removing the solvent, the crude product is purified by column chromatography (13.4 g, 59% yield, 95% purity, log P (pH 2.3)=2.02).

Source