Methylamine → HCID 19353513, compound

HRID 378304Notes

Reaction equation

HRID 378304 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([Cl:18])[N:15]=[C:14](Cl)[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:20][NH2:21].[ClH:22].CO>CO.C(OCC)C>[ClH:18].[ClH:22].[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]([Cl:18])[CH:17]=2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6329MethylamineHCID 19353488HCID 19353488, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 19353513HCID 19353513, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

0.11 g (0.00035 mol) of 4-amino-N-(2,6-dichloro-pyridin-4-yl)-benzenesulfonamide was stirred in 25 ml of liquid methylamine in an autoclave at 130° C. for 72 hours. After removal of the methylamine the residue was taken up in 5 ml of dichloromethane/methanol 1:1, filtered and, after removal of the solvent, chromatographed on silica gel with hexane/ethyl acetate 3:1, 2:1 and finally 1:1. The product, obtained as a white, amorphous solid substance, was dissolved in 2 ml of methanol, treated with 2 ml of 2N HCl/methanol, diluted with 20 ml of diethyl ether and filtered off under suction. The material on the suction filter was washed well with diethyl ether and dried in a high vacuum. There was obtained 0.055 g (41%) of 4-amino-N-(2-chloro-6-methylamino-pyridin-4-yl)-benzenesulfonamide dihydrochloride (1:2) as white crystals; m.p.: >215° C. (dec.).

Workup

  1. customAfter removal of the methylamine the residue
  2. filtrationfiltered
  3. customafter removal of the solvent
  4. customchromatographed on silica gel with hexane/ethyl acetate 3:1, 2:1 and finally 1:1
  5. customThe product, obtained as a white, amorphous solid substance
  6. filtrationfiltered off under suction
  7. filtrationThe material on the suction filter
  8. washwas washed well with diethyl ether
  9. customdried in a high vacuum

Sources & evidence

ORD record
ord-ccd3a72c58d04c68936400869d464a74
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

Loading…