Methanol → 2-(Chloromethyl)-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide
Reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]=[C:10]=[O:11])[N:3]=1.[Cl:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([NH2:23])(=[O:22])=[O:21].[CH3:24][O-:25].[Na+].[OH2:27].[CH3:28]O>C(#N)C>[Cl:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[S:20]([NH:23][C:10]([NH:9][C:4]1[N:5]=[C:6]([O:25][CH3:24])[N:7]=[C:2]([O:27][CH3:28])[N:3]=1)=[O:11])(=[O:22])=[O:21]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4,6-dichloro-1,3,5-triazin-2-yl isocyanate (3.10 g, 16.2 mmol) in acetonitrile (15 ml) was contacted with 2-(chloromethyl)benzene sulfonamide (3.34 g, 16.2 mmol) and stirred for 20 hrs at 25°. The mixture was heated at 50° for 2 hrs, cooled and filtered to provide 3.86 g, mp 162°-170°, which was contacted with sodium methoxide (30 mmol) in methanol (60 ml) at 20°-25° for 16 hrs. Water (100 ml) was added and the mixture was filtered and neutralized by addition of hydrochloride acid. Filtration and drying gave 2.20 g of white solid, mp 150°-152° (dec.). 1H nmr δDMSO-d6TMS 11.0 (s), 8.30-7.50 (m), 5.23 (s), 4.03 (s). IR nujol) featured absorption bands centered at 3200, 1720, 1610 and 1560 cm-1.
Workup
- temperatureThe mixture was heated at 50° for 2 hrs
- temperaturecooled
- filtrationfiltered
- customto provide 3.86 g, mp 162°-170°, which
- filtrationthe mixture was filtered
- additionneutralized by addition of hydrochloride acid
- filtrationFiltration
- customdrying
Sources & evidence
- ORD record
- ord-e3f81eb409d2431c8e14cd850aef493f
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04723990
Reaction notes
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