반응 #1255004

반응 방정식

bromo-acetonitrile

DBU

4-(aminosulfonyl)phenylisothiocyanate

cyanamide

DBU

→

2-(4-aminosulfonylphenyl)amino-4-amino-thiazole-5-carbonitrile

수율 49.4%

용매

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred overnight at room temperature
2. 2
   기타the solvent was removed at the reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in EtOAc (200 ml)
4. 4
   세척The EtOAc solution was washed with 0.1 N HCl (150 ml×3) and brine
5. 5
   건조dried with MgSO4
6. 6
   농축concentrated
7. 7
   기타The residue was purified by silica gel chromatography (EtOAc)

실험 절차

To a solution of 4-(aminosulfonyl)phenylisothiocyanate (1.12 g, 5.0 mmol) and cyanamide (0.23 g, 5.5 mmol) in acetonitrile (50 ml) was added DBU (0.83 g, 5.5 mmol), and the resulting mixture was stirred at room temperature for 60 minutes. To the reaction mixture was added bromo-acetonitrile (0.66 g, 5.5 mmol) followed by DBU (0.83 g, 5.5 mmol) 30 minutes afterward. The reaction mixture was stirred overnight at room temperature, the solvent was removed at the reduced pressure, and the residue was dissolved in EtOAc (200 ml). The EtOAc solution was washed with 0.1 N HCl (150 ml×3) and brine and dried with MgSO4 and concentrated. The residue was purified by silica gel chromatography (EtOAc) to provide 0.73 g (48%) of 2-(4-aminosulfonylphenyl)amino-4-amino-thiazole-5-carbonitrile.

출처