反応 #440933

反応方程式

2-bromo-1-(3-methylsulfanyl-phenyl)ethanone

1-(4-isothiocyanatophenyl)-4-methylpiperazine

cyanamide

potassium tert-butoxide

→

[4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazoly](3-methylsulfanyl-phenyl)methanone

収率 50.0%

溶媒

ethyl acetate

acetonitrile

t-butanol

反応条件

後処理

1. 1
   workup.ADDITION0.49 g, 2.0 mmol) was added
2. 2
   温度refluxed for 15 minutes
3. 3
   洗浄washed in turn with saturated aqueous sodium carbonate and brine
4. 4
   乾燥The dried (sodium sulfate) solution
5. 5
   その他was evaporated
6. 6
   その他the residue chromatographed on silica gel
7. 7
   洗浄Elution of the desired product
8. 8
   その他with 9:1 dichloromethane/methanol and crystallization from ethyl acetate/hexane

実験手順

To a mixture of 1-(4-isothiocyanatophenyl)-4-methylpiperazine (of Example 1; 0.466 g, 2.0 mmol) and cyanamide (0.088 g, 2.1 mmol) in acetonitrile (3 mL) and t-butanol (5 ml), a solution of potassium tert-butoxide (2.0 mL, 1.0 M in tert-BuOH) was added. After 30 minutes at room temperature, 2-bromo-1-(3-methylsulfanyl-phenyl)ethanone (which can be prepared by the procedure of Rogers, N. H. et. al. EP 87953; 0.49 g, 2.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 hour and then refluxed for 15 minutes. The cooled mixture was diluted with ethyl acetate and washed in turn with saturated aqueous sodium carbonate and brine. The dried (sodium sulfate) solution was evaporated and the residue chromatographed on silica gel. Elution of the desired product with 9:1 dichloromethane/methanol and crystallization from ethyl acetate/hexane provided 0.439 g (50% yield) of [4-amino-2-[[4-(4-methyl-1-piperazinyl)phenyl]amino]-5-thiazoly](3-methylsulfanyl-phenyl)methanone. Mass spectrum (ES) MH+=440.

出典