Reaction #833509

Reaction equation

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

1,3-propane sultone

tetrahydrofuran

→

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

Yield 99.7%

Solvents

1-methyl-2-pyrrolidinone

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 resulting dye is recrystallized from methanol/ethyl acetate

Procedure

0.5 g (1.5 mmol) of N,N-dimethyl-4-[1,3-thiazol-2-yldiazenyl]aniline are dissolved in 1-methyl-2-pyrrolidinone (NMP), and 0.9 g (7.5 mmol) of 1,3-propane sultone is added. The reaction mixture is heated at, 100° C. for 4 hours. After cooling, 20 ml of tetrahydrofuran are added to the reaction mixture and the precipitated product is filtered off, washed with acetone and dried. The resulting dye is recrystallized from methanol/ethyl acetate. 0.53 g (45% of theory) of 3-(2-{[4-(dimethylamino)phenyl]diazenyl}-1,3-thiazol-3-ium-3-yl)-1-propanesulfonate is obtained as a dark blue powder.

Source