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 1762053Notes

Reaction equation

HRID 1762053 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 of 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-054440d06edd4869961a6d845a429489
Source dataset
uspto-grants-1989_05
Patent number
US04830662

Reaction notes

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