Methylamine → HCID 10689660, compound

HRID 378305Notes

Reaction equation

HRID 378305 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([Br:18])[N:15]=[C:14](Br)[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:20][NH2:21]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2[CH:13]=[C:14]([NH:21][CH3:20])[N:15]=[C:16]([Br:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6329Methylamine2×HCID 108113474-amino-N-(2,6-dibromo-pyridin-4-yl)-benzenesulfonamide

Product 1

HCID 10689660HCID 10689660, compoundYield 88%

Procedure

0.81 g (0.002 mol) of 4-amino-N-(2,6-dibromo-pyridin-4-yl)-benzenesulfonamide was stirred in 35 ml of liquid methylamine in an autoclave at 130° C. for 44 hours. The methylamine was left to evaporate, the residue was dissolved in ethanol, treated with 2 g of silica gel, concentrated and the residue was chromatographed on silica gel, firstly with ethyl acetate/hexane 1:2, then with pure ethyl acetate. There was obtained 0.63 g (88%) of 4-amino-N-(2-bromo-6-methylamino-pyridin-4-yl)-benzenesulfonamide as a beige foam. 0.33 g (0.00092 mol) of this was dissolved in 10 ml of methanol, treated with 5 ml of 2M HCl in methanol, concentrated and again treated with 4 ml of methanol. The precipitate obtained was filtered off under suction, rinsed with a small amount of methanol and dried in a high vacuum. There was obtained 0.27 g (69%) of 4-amino-N-(2-bromo-6-methylamino-pyridin-4-yl)-benzenesulfonamide hydrochloride as white crystals; m.p.: 226-228° C. (dec.).

Workup

  1. customto evaporate
  2. dissolutionthe residue was dissolved in ethanol
  3. additiontreated with 2 g of silica gel
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel, firstly with ethyl acetate/hexane 1:2

Sources & evidence

ORD record
ord-61f4ce0e43c2436baf6b254ac27dac52
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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