Dabco → N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,6-dichlorobenzenesulfonamide

HRID 127812Notes

Reaction equation

HRID 127812 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([NH:10][CH3:11])[N:4]=1.N12CCN(CC1)CC2.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[S:28]([N:31]=[C:32]=[O:33])(=[O:30])=[O:29]>C(#N)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([N:10]([CH3:11])[C:32]([NH:31][S:28]([C:22]2[C:23]([Cl:27])=[CH:24][CH:25]=[CH:26][C:21]=2[Cl:20])(=[O:29])=[O:30])=[O:33])[N:4]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 13766724-methoxy-N,6-dimethylpyrimidin-2-amineHCID 128751892,6-Dichlorobenzenesulfonyl isocyanate

Product 1

HCID 12875190N-[N-(4-methoxy-6-methylpyrimidine-2-yl)-N-methylaminocarbonyl]-2,6-dichlorobenzenesulfonamideYield 23.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 0.8 g of 4-methoxy-6-methyl-2-methylaminopyrimidine in 25 ml of dry acetonitrile containing a few crystals of 1,4-diazabicyclo[2.2.2]octane was added 1.3 g of 2,6-dichlorobenzenesulfonyl isocyanate. The mixture was stirred at ambient temperature for 16 hours and the resultant solution was evaporated leaving a white solid. Trituration with 1-chlorobutane followed by filtration afforded 0.5 g of N-[N-(4-methoxy-6-methylpyrmidine-2-yl)-N-methylaminocarbonyl]-2,6-dichlorobenzenesulfonamide melting at 170°-171°. Infrared absorption peaks were observed at 1700 cm-1, 1600 cm-1, and 1570 cm-1.

Workup

  1. customthe resultant solution was evaporated
  2. customleaving a white solid
  3. filtrationTrituration with 1-chlorobutane followed by filtration

Sources & evidence

ORD record
ord-afbee4250d9f4bdebdb917dd0ea30e39
Source dataset
uspto-grants-1981_03
Patent number
US04257802

Reaction notes

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