2-Amino-4-methoxy-6-methyl-1,3,5-triazine → N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamide

HRID 1732720Notes

Reaction equation

HRID 1732720 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[Cl:11][CH2:12][CH2:13][O:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]([N:26]=[C:27]=[O:28])(=[O:25])=[O:24])=[O:16]>C(Cl)Cl>[CH3:9][O:8][C:6]1[N:5]=[C:4]([CH3:10])[N:3]=[C:2]([NH:1][C:27]([NH:26][S:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:15]([O:14][CH2:13][CH2:12][Cl:11])=[O:16])(=[O:24])=[O:25])=[O:28])[N:7]=1

Participants

4

Reactant 2

HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 139205492-(beta-Chloroethoxycarbonyl)benzenesulfonylisocyanate

Product 1

HCID 13176696N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.7 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(β-chloroethoxycarbonyl)benzenesulfonyl isocyanate with stirring at ambient temperature. The mixture was thereafter stirred for sixteen hours. The solvent was evaporated under reduced pressure and the residue triturated with hexane and filtered to yield 1.72 g of compound which melted at 167°-170° C. The solid showed infrared absorption peaks at 1700 and 1705 cm-1, consistent for N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamide.

Workup

  1. stirringThe mixture was thereafter stirred for sixteen hours
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue triturated with hexane
  4. filtrationfiltered

Sources & evidence

ORD record
ord-f1fdf8588a32494eb68ee0114e5ae27a
Source dataset
uspto-grants-1980_12
Patent number
US04238621

Reaction notes

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