Isopropanol → (1-Methylethyl) [3-[[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]aminosulfonyl]phenyl]carbamate
Reaction equation
N(C1C=C(S(N=C=O)(=O)=O)C=CC=1)=C=O.NC1N=C(OC)C=C(C)N=1.[N:26]([C:29]1[CH:30]=[C:31]([S:35]([NH:38][C:39]([NH:41][C:42]2[N:47]=[C:46]([O:48][CH3:49])[CH:45]=[C:44]([CH3:50])[N:43]=2)=[O:40])(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1)=[C:27]=[O:28].[CH3:51][CH:52]([OH:54])[CH3:53]>C(Cl)Cl>[CH3:49][O:48][C:46]1[CH:45]=[C:44]([CH3:50])[N:43]=[C:42]([NH:41][C:39]([NH:38][S:35]([C:31]2[CH:30]=[C:29]([NH:26][C:27](=[O:28])[O:54][CH:52]([CH3:53])[CH3:51])[CH:34]=[CH:33][CH:32]=2)(=[O:37])=[O:36])=[O:40])[N:47]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To an anhydrous solution of 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]benzenesulfonamide, 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
- filtrationFiltration of the reaction mixture and evaporation of the filtrate
Sources & evidence
- ORD record
- ord-43743f733122421eaa4b7bf0155caea8
- Source dataset
- uspto-grants-1983_01
- Patent number
- US04369058
Reaction notes
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