4,6-dimethoxy-N-methyl-1,3,5-triazin-2-amine → N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:14]=[C:15]=[O:16])(=[O:13])=[O:12])(=[O:4])=[O:3].[CH3:17][NH:18][C:19]1[N:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21]([O:27][CH3:28])[N:20]=1>C(Cl)Cl>[CH3:26][O:25][C:23]1[N:22]=[C:21]([O:27][CH3:28])[N:20]=[C:19]([N:18]([CH3:17])[C:15]([NH:14][S:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:2]([CH3:1])(=[O:3])=[O:4])(=[O:12])=[O:13])=[O:16])[N:24]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-methylsulfonylbenzenesulfonylisocyanate (2.1 g, 8.0 mmol) in dry methylene chloride (12 ml) was added to 2-methylamino-4,6-dimethoxy-1,3,5-triazine (1.0 g, 6.0 mmol) and a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane. The mixture was stirred at room temperature overnight. The solvent was removed in-vacuo and 1-chlorobutane was added to the residue. The precipitated solid was filtered and dried to give N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)(methyl)aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide (2.3 g) as a white powder, m.p. 160°-162.5°. The product showed characteristic singlets in the NMR at δ3.25 (NCH3), 3.40 (SO2CH3) and 4.0 (OCH3), and showed infrared absorption peaks at 1690, 1550, 1420, 1340, 1310 and 1150 cm-1.
Workup
- customThe solvent was removed in-vacuo and 1-chlorobutane
- additionwas added to the residue
- filtrationThe precipitated solid was filtered
- customdried
Sources & evidence
- ORD record
- ord-698cdc1f07524796ac08749a23944a5a
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04655822
Reaction notes
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