Reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]=[C:14]=[O:15])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)=[C:2]=[O:3].[NH2:16][C:17]1[N:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([CH3:25])[N:18]=1.[CH3:26][CH:27]([OH:29])[CH3:28]>C(Cl)Cl>[CH3:24][O:23][C:21]1[CH:20]=[C:19]([CH3:25])[N:18]=[C:17]([NH:16][C:14]([NH:13][S:10]([C:6]2[CH:5]=[C:4]([NH:1][C:2](=[O:3])[O:29][CH:27]([CH3:28])[CH3:26])[CH:9]=[CH:8][CH:7]=2)(=[O:11])=[O:12])=[O:15])[N:22]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To an anhydrous solutiion o 2.3 g of m-isocyanatobenzenesulfonyl isocyanate in 50 ml of methylene chloride was added in small portions 1.4 g of 2-amino-4-methoxy-6-methylpyrimidine. Efficient stirring was maintained during the addition and for three additional hours. The intermediate thus obtained, 3-isocyanato-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benenesulfonamide, was reacted further by adding one gram of 2-propanol and stirring the resultant mixture for an additional sixteen hours. Filtration of the reaction mixture and evaporation of the filtrate yielded the desired product melting at 173°-180°.
Workup
- temperaturewas maintained during the addition and for three additional hours
- customThe intermediate thus obtained
- custom3-isocyanato-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benenesulfonamide, was reacted further
- filtrationFiltration of the reaction mixture and evaporation of the filtrate
Sources & evidence
- ORD record
- ord-117ab8697f8f439cae2eb0a9f17a5622
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04225337
Linked notes
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