Methylamine → HCID 11024311, compound

HRID 1603558Notes

Reaction equation

HRID 1603558 reaction equation
Br[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Br:18])[N:3]=1.[CH3:19][NH2:20]>O1CCOCC1.C(O)C>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:5]=[C:4]([Br:18])[N:3]=[C:2]([NH:20][CH3:19])[CH:7]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 11024311HCID 11024311, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1.45 g (0.0037 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine were dissolved in 40 ml of dioxane and treated with 9.6 ml of 8M methylamine in ethanol. The mixture was stirred at room temperature for 48 hrs., the solvents were removed and the residue was chromatographed on silica gel with ethyl acetate/hexane 1:3 and 1:2. The product-containing fractions, after concentration, were suspended in 50 ml of diethyl ether, treated in an ultrasound bath for 1 hr., then treated with 75 ml of hexane and the precipitate which thereby resulted was filtered off under suction. After drying in a high vacuum there was obtained 0.87 g (69%) of [4-(4-aminobenzenesulphonyl)-6-bromopyridin-2-yl]-methylamine as pale beige crystals; m.p.: 171-173° C.

Workup

  1. custom, the solvents were removed
  2. customthe residue was chromatographed on silica gel with ethyl acetate/hexane 1:3 and 1:2
  3. concentrationThe product-containing fractions, after concentration
  4. additiontreated in an ultrasound bath for 1 hr
  5. addition, then treated with 75 ml of hexane
  6. customthe precipitate which thereby resulted
  7. filtrationwas filtered off under suction
  8. customAfter drying in a high vacuum there

Sources & evidence

ORD record
ord-af8a4e2a506640f6832dc4d231b0334c
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…