Cyanamide → 2-(4-Aminosulfonylphenyl)amino-4-amino-thiazole-5-carbonitrile
Reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]=[S:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N:14]#[C:15][NH2:16].C1CCN2[C:20](=[N:21]CCC2)[CH2:19]C1.BrCC#N>C(#N)C>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]2[S:13][C:19]([C:20]#[N:21])=[C:15]([NH2:16])[N:14]=2)=[CH:9][CH:10]=1)(=[O:4])=[O:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- stirringThe reaction mixture was stirred overnight at room temperature
- customthe solvent was removed at the reduced pressure
- dissolutionthe residue was dissolved in EtOAc (200 ml)
- washThe EtOAc solution was washed with 0.1 N HCl (150 ml×3) and brine
- dry with materialdried with MgSO4
- concentrationconcentrated
- customThe residue was purified by silica gel chromatography (EtOAc)
Sources & evidence
- ORD record
- ord-a846c747fc21416ebcf8cc3c852d28d7
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06620828B2
Reaction notes
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