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

HRID 485515Notes

Reaction equation

HRID 485515 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.[CH:12]([O:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24]([N:27]=[C:28]=[O:29])(=[O:26])=[O:25])=[O:17])([CH3:14])[CH3:13]>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:28]([NH:27][S:24]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:16]([O:15][CH:12]([CH3:14])[CH3:13])=[O:17])(=[O:26])=[O:25])=[O:29])[N:7]=1

Participants

4

Reactant 2

HCID 278402-Amino-4,6-dimethoxy-1,3,5-triazineHCID 13305294Propan-2-yl 2-[(oxomethylidene)sulfamoyl]benzoate

Product 1

HCID 13176697N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(isopropoxycarbonyl)benzenesulfonamideYield 26.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0.7 g of 2-amino-4,6-dimethoxy-1,3,5-triazine suspended in 5.0 ml anhydrous methylene chloride was added 1.6 g of 2-isopropoxycarbonylbenzenesulfonyl isocyanate in 5.0 ml anhydrous methylene chloride. The resulting mixture was filtered to remove some unreacted 2-amino-4,6-dimethoxytriazine, the methylene chloride filtrate was evaporated at reduced pressure and the residue triturated with chlorobutane to yield 0.5 g of desired product melting at 192°-195° C. The solid showed infrared absorption peaks at 1705 and 1715 cm-1 consistent for N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(isopropoxycarbonyl)benzenesulfonamide.

Workup

  1. filtrationThe resulting mixture was filtered
  2. customto remove some unreacted 2-amino-4,6-dimethoxytriazine
  3. customthe methylene chloride filtrate was evaporated at reduced pressure
  4. customthe residue triturated with chlorobutane

Sources & evidence

ORD record
ord-7cec4a38c05a4fb6a95e3448775623f8
Source dataset
uspto-grants-1985_08
Patent number
US04536576

Reaction notes

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