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

HRID 1732719Notes

Reaction equation

HRID 1732719 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][CH2:13][CH2:14][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]>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][CH2:14][CH2:13][Cl:12])=[O:17])(=[O:25])=[O:26])=[O:29])[N:7]=1

Participants

4

Reactant 2

HCID 278402-Amino-4,6-dimethoxy-1,3,5-triazineHCID 139205492-(beta-Chloroethoxycarbonyl)benzenesulfonylisocyanate

Product 1

HCID 13176695N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-(2-chloroethoxycarbonyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.7 g of 2-amino-4,6-dimethoxy-1,3,5-triazine in 10 ml anhydrous methylene chloride solvent was added 1.45 g 2-(β-chloroethoxycarbonyl)benzenesulfonyl isocyanate. After stirring at ambient temperature for sixteen hours the solvent was removed under reduced pressure, the residue triturated with ether and the solid product filtered off, yield 1.21 g, m.p. 171°-174° 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-(2-chloroethoxycarbonyl)benzenesulfonamide.

Workup

  1. customwas removed under reduced pressure
  2. customthe residue triturated with ether
  3. filtrationthe solid product filtered off
  4. customabsorption peaks at 1705 and 1715 cm-1

Sources & evidence

ORD record
ord-fd2701cc7f7e47939619b53dd87135e0
Source dataset
uspto-grants-1980_12
Patent number
US04238621

Reaction notes

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