Reaction #674320

ord-845ce6ba1a8e45dd8da4c4971f129d4e

Reaction equation

NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
A1
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide
Clc1ncnc(Cl)n1
2,4-dichloro-1,3,5-triazine
Nc1cccc(S(N)(=O)=O)c1
3-aminobenzenesulfonamide
→
NS(=O)(=O)c1cccc(Nc2ncnc(Cl)n2)c1
desired product A2
Yield 35.0%
NS(=O)(=O)c1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenesulfonamide
Yield 35.0%

Reactants

NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
A1
NS(=O)(=O)Cc1cccc(Nc2ncnc(Cl)n2)c1
3-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide
Clc1ncnc(Cl)n1
2,4-dichloro-1,3,5-triazine
Nc1cccc(S(N)(=O)=O)c1
3-aminobenzenesulfonamide

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherA2 was prepared
  2. 2
    OtherThe crude product was purified by flash chromatography on silica gel (cHex/EtOAc=20:1 to 1:20)

Procedure

A2 was prepared following the general procedure reported for A1 using 2,4-dichloro-1,3,5-triazine and 3-aminobenzenesulfonamide as reacting agents. The crude product was purified by flash chromatography on silica gel (cHex/EtOAc=20:1 to 1:20) to yield the desired product A2 as a white solid (35%). 1H NMR (400 MHz, d6-DMSO, 300K) δ 7.41 (s, 2H), 7.59 (m, 2H), 7.85 (d, J=6.9 Hz, 1H), 8.21 (br.s, 1H), 8.69 (s, 1H), 11.02 (s, 1H). MS (ES) C9H8ClN5O2S requires: 285. found: 286 (M+H)+.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09226929B2uspto-grants-2016_01