Citric Acid → HCID 18704828, compound

HRID 343382Notes

Reaction equation

HRID 343382 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:16][C:17]1[N:18]=[N:19][C:20](Cl)=[CH:21][CH:22]=1)(=[O:15])=[O:14].[CH3:25][S-:26].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:1][N:2]([CH3:24])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:16][C:17]1[N:18]=[N:19][C:20]([S:26][CH3:25])=[CH:21][CH:22]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4378561Sodium methanethiolateHCID 11793037HCID 11793037, compound

Product 1

HCID 18704828HCID 18704828, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Dimethylamino-N-(6-chloro-3-pyridazinyl)-1-naphthalenesulphonamide (0.72 g) was dissolved in N,N-dimethylformamide and sodium thiomethoxide (0.42 g) added. The mixture was heated to 100° C. for 6 hours, then cooled and 7% aqueous citric acid solution (15 ml) was added with stirring. The solid formed was collected by filtration and washed with water (10 ml). The solid was then purified by chromatography on silica gel (20 g) under reduced pressure, eluting with an ethyl acetate/toluene gradient, to give 5-dimethylamino-N-(6-methylthio-3-pyridazinyl)-1-naphthalenesulphonamide (0.28 g), m.p. 188°-190° C.; mass spectrum (+ve CI): 375 (M+H)+.

Workup

  1. temperaturecooled
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water (10 ml)
  5. customThe solid was then purified by chromatography on silica gel (20 g) under reduced pressure
  6. washeluting with an ethyl acetate/toluene gradient

Sources & evidence

ORD record
ord-e785878bb1ae4f9091c12deb31e45869
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

Loading…