2-(1-methyl-1H-pyrazol-4-yl)benzenesulfonamide → N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(1-methyl-1H-pyrazol-4-yl)benzenesulfonamide

HRID 1980787Notes

Reaction equation

HRID 1980787 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[S:13]([NH2:16])(=[O:15])=[O:14])[CH:4]=[N:3]1.C[Al](C)C.[CH3:21][O:22][C:23]1[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH:30][C:31](=O)[O:32]C)[N:24]=1>C(Cl)Cl>[CH3:21][O:22][C:23]1[N:28]=[C:27]([CH3:29])[N:26]=[C:25]([NH:30][C:31]([NH:16][S:13]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)(=[O:15])=[O:14])=[O:32])[N:24]=1

Participants

5

Reactant 3

HCID 134898142-(1-methyl-1H-pyrazol-4-yl)benzenesulfonamideHCID 14404501Methyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamateHCID 16682925Trimethylaluminum

Product 1

HCID 13489865N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-(1-methyl-1H-pyrazol-4-yl)benzenesulfonamideYield 17.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

By the procedure of Example 14, 2 g of 2-(1-methyl-1H-pyrazol-4-yl)benzenesulfonamide, prepared in Example 19, was reacted in 100 ml of methylene chloride with 0.7 g of trimethylaluminum (5 ml of 2M toluene solution) followed by 1.7 g of methyl (4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamate. After work up and evaporation of the methylene chloride solvent, the residue was triturated with ethyl acetate to yield 0.6 g of the title compound; m.p. 221°-224° C. The IR spectrum showed a carbonyl absorption at 1700 cm-1 indicative for a sulfonylurea.

Workup

  1. customAfter work up and evaporation of the methylene chloride solvent
  2. customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-70198f55f61f447c819e7aa38bdd886a
Source dataset
uspto-grants-1985_04
Patent number
US04511392

Reaction notes

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