Methylamine → (4-Benzenesulphonyl-6-bromopyridin-2-yl)-methylamine

HRID 1603549Notes

Reaction equation

HRID 1603549 reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[C:14]([Br:16])[N:13]=[C:12](Br)[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][NH2:19]>C(O)C.O1CCOCC1>[C:1]1([S:7]([C:10]2[CH:15]=[C:14]([Br:16])[N:13]=[C:12]([NH:19][CH3:18])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 541123304-Benzenesulphonyl-2,6-dibromopyridine

Product 1

HCID 15410397(4-Benzenesulphonyl-6-bromopyridin-2-yl)-methylamineYield 61%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

0.42 g (0.00112 mol) of 4-benzenesulphonyl-2,6-dibromopyridine and 1.4 ml of 8M methylamine in ethanol were stirred at room temperature in a mixture of 11 ml of ethanol and 11 ml of dioxane for 48 hrs. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:10. The product-containing fractions were suspended in 25 ml of diethyl ether, treated in an ultrasound bath and diluted with 45 ml of hexane. The suspension was suction filtered and the filter material was dried in a high vacuum. There was obtained 0.224 g (61%) of (4-benzenesulphonyl-6-bromopyridin-2-yl)-methylamine as white crystals; m.p.: 145-148° C.

Workup

  1. customAfter removal of the solvent the residue
  2. customwas chromatographed on silica gel with ethyl acetate/hexane 1:10
  3. additiontreated in an ultrasound bath
  4. additiondiluted with 45 ml of hexane
  5. filtrationsuction filtered
  6. customthe filter material was dried in a high vacuum

Sources & evidence

ORD record
ord-5e5ad1c6e525466d9b5a1d3fe4fcec69
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…