Methylamine → HCID 19605448, compound

HRID 1603606Notes

Reaction equation

HRID 1603606 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]([CH3:18])[N:3]=1.[CH3:19][NH2:20]>C(O)C.O1CCOCC1>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:5]=[C:4]([CH3:18])[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 19605507HCID 19605507, compound

Product 1

HCID 19605448HCID 19605448, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

0.056 g (0.00017 mol) of 4-(2-bromo-6-methylpyridine-4-sulphonyl)-phenylamine and 1.1 ml of 8 M methylamine in ethanol were stirred at 120° C. in 5 ml of dioxane for 24 hrs. After removal of the solvent the residue was chromatographed on silica gel with ethyl acetate/hexane 1:1. The product-containing fraction 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 0.04 g (84%) of [4-(4-aminobenzenesulphonyl)-6-methyl-pyridin-2-yl]-methylamine as light yellow crystals; m.p.: 126-127° C.

Workup

  1. customAfter removal of the solvent the residue
  2. customwas chromatographed on silica gel with ethyl acetate/hexane 1:1
  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-d47a91ba8af84dba99584a13cbfd0ee9
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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