2-Amino-4,6-dimethoxy-1,3,5-triazine → N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide

HRID 1704612Notes

Reaction equation

HRID 1704612 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[N:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[S:19]([N:22]=[C:23]=[O:24])(=[O:21])=[O:20]>C(Cl)Cl>[CH3:9][O:8][C:6]1[N:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([NH:1][C:23]([NH:22][S:19]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[Cl:12])(=[O:20])=[O:21])=[O:24])[N:7]=1

Participants

4

Reactant 2

HCID 278402-Amino-4,6-dimethoxy-1,3,5-triazineHCID 174071Benzenesulfonyl isocyanate, 2-chloro-

Product 1

HCID 14835175N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 15.6 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 300 ml of dry methylene chloride containing 0.1 g 1,4-diazabicyclo[2,2,2]octane was added 21 g 2-chlorobenzenesulfonyl isocyanate with stirring. The mixture was stirred for 16 hours and the resultant solid was removed by filtration. After washing the solid with 1-chlorobutane, the resulting product, N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)-aminocarbonyl]-2-chlorobenzenesulfonamide melted at 188°-189° C. Infrared absorption analysis showed absorption peaks at 1740 cm-1, 1630 cm-1 and 1595 cm-1 which are typical for this type of compound.

Workup

  1. stirringThe mixture was stirred for 16 hours
  2. customthe resultant solid was removed by filtration
  3. washAfter washing the solid with 1-chlorobutane
  4. customabsorption analysis
  5. customabsorption peaks at 1740 cm-1, 1630 cm-1 and 1595 cm-1 which

Sources & evidence

ORD record
ord-3f5511fb26d5403e9c89d6032cc99f9b
Source dataset
uspto-grants-1978_11
Patent number
US04127405

Reaction notes

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