반응 #10909

반응 방정식

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-thiazolyl](3-methylsulfanyl-phenyl)methanone

수율 50.0%

용매

ethyl acetate

acetonitrile

t-butanol

반응 조건

후처리

1. 1
   workup.ADDITION0.49 g, 2.0 mmol) was added
2. 2
   온도refluxed for 15 minutes
3. 3
   세척washed in turn with saturated aqueous sodium carbonate and brine
4. 4
   건조The dried (sodium sulfate) solution
5. 5
   기타was evaporated
6. 6
   기타the residue chromatographed on silica gel
7. 7
   세척Elution of the desired product
8. 8
   기타with 9:1 dichloromethane/methanol and crystallization from ethyl acetate/hexane

실험 절차

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-thiazolyl](3-methylsulfanyl-phenyl)methanone. Mass spectrum (ES) MH+=440.

출처