2-Aminomethyl-4,6-dimethoxy-1,3,5-triazine → N'-[(4,6-dimethoxy-1,3,5-triazin-2-yl)methylaminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide
Reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12]([N:15]=[C:16]=[O:17])(=[O:14])=[O:13])(=[O:5])=[O:4].[NH2:19][CH2:20][C:21]1[N:26]=[C:25]([O:27][CH3:28])[N:24]=[C:23]([O:29][CH3:30])[N:22]=1>C(#N)C>[CH3:28][O:27][C:25]1[N:24]=[C:23]([O:29][CH3:30])[N:22]=[C:21]([CH2:20][NH:19][C:16]([NH:15][S:12]([C:7]2[C:6]([S:3]([N:2]([CH3:18])[CH3:1])(=[O:4])=[O:5])=[CH:11][CH:10]=[CH:9][CH:8]=2)(=[O:13])=[O:14])=[O:17])[N:26]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1.3 g of 2-(N,N-dimethylsulfamoyl)-benzenesulfonyl isocyanate in 25 ml of dry acetonitrile was treated at room temperature with 0.58 g of the product from Example 4. The resulting suspension was heated to 50°-55° C. for 11/2 hours and was then stirred at room temperature for an additional 15 hours. The solution was filtered and the collected solid washed well with 1-chlorobutane and then dried to yield 0.96 g of N'-[(4,6-dimethoxy-1,3,5-triazin-2-yl)methylaminocarbonyl]-N,N-dimethyl-1,2-benzenedisulfonamide as a light yellow powder, m.p. 183°-189° C., contaminated with some of the unreacted heterocyclic amine. Stirring the crude product with 5% hydrochloric acid at room temperature for 15 minutes followed by filtration gave the pure product as a white powder, m.p. 199°-201° C.
Workup
- temperatureThe resulting suspension was heated to 50°-55° C. for 11/2 hours
- filtrationThe solution was filtered
- washthe collected solid washed well with 1-chlorobutane
- customdried
Sources & evidence
- ORD record
- ord-45e437ca06f8496f93117985f5cd0d68
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04565567
Reaction notes
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