Reaction #10895

Reaction equation

2-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone

1-(4-isothiocyanatophenyl)-4-methyl piperazine

1-(4-isothiocyanatophenyl)-4-methylpiperazine

cyanamide

Potassium t-butoxide

→

[4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](2,3-dihydro-1,4-benzodioxin-6-yl)methanone

Yield 66.0%

Solvents

acetonitrile

tert-Butanol

Conditions

Workup

1. 1
   workup.STIRRINGthe solution was stirred at room temperature for 3 days
2. 2
   FiltrationThe yellow solid was filtered off
3. 3
   Washwashed with cold acetonitrile

Procedure

tert-Butanol (4 mL) and then 1-(4-isothiocyanatophenyl)-4-methyl piperazine (of Example 1; 219 mg, 1 mmol) were added to a solution of cyanamide (44 mg, 1.05 mmol) (Aldrich) in acetonitrile (5 mL). Potassium t-butoxide (1 M in tert-butanol; 1 mL, 1 mmol) was added and the solution was stirred for 30 min. 2-Bromo-1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone (257 mg, 1 mmol) (Maybridge Chemical Company Ltd.) was added, and the solution was stirred at room temperature for 3 days. The yellow solid was filtered off and washed with cold acetonitrile and then ether to give [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazolyl](2,3-dihydro-1,4-benzodioxin-6-yl)methanone (280 mg, 66%).

Source