Reaction #833508

Reaction equation

N,N-dimethyl-4-[1,3-thiazol-2-yldiazenyl]aniline

butane sultone

→

4-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate

Yield 87.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   TemperatureAfter cooling
2. 2
   Filtrationthe precipitated product is filtered off
3. 3
   Washwashed with acetone
4. 4
   Otherdried
5. 5
   OtherThe dye is recrystallized with methanol/ethyl acetate

Procedure

8.5 g (36.6 mmol) of N,N-dimethyl-4-[1,3-thiazol-2-yldiazenyl]aniline are heated with 85 ml of butane sultone at 110° C. for 6 hours. After cooling, 200 ml of tetrahydrofuran are added to the reaction mixture and the precipitated product is filtered off, washed with acetone and dried. The dye is recrystallized with methanol/ethyl acetate. 11.8 g (87% of theory) of 4-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-butanesulfonate are obtained as a dark blue power.

Source