Citric Acid → 5-dimethylamino-N-(6-chloro-5-methyl-3-pyridazinyl)-1-naphthalenesulphonamide

HRID 343380Notes

Reaction equation

HRID 343380 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:5]=[N:6][C:7]([Cl:11])=[C:8]([CH3:10])[CH:9]=1.[CH3:12][N:13]([CH3:28])[C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[C:19]2[S:24](Cl)(=[O:26])=[O:25].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>COCCOC>[CH3:12][N:13]([CH3:28])[C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16]=[CH:17][CH:18]=[C:19]2[S:24]([NH:3][C:4]1[N:5]=[N:6][C:7]([Cl:11])=[C:8]([CH3:10])[CH:9]=1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 11801Dansyl chlorideHCID 24758Sodium hydrideHCID 123536636-Chloro-5-methylpyridazin-3-amine

Product 1

HCID 105957285-dimethylamino-N-(6-chloro-5-methyl-3-pyridazinyl)-1-naphthalenesulphonamideYield 21.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.25 g) was added to a solution of 3-amino-6-chloro-5-methylpyridazine (0.36 g) in dry 1,2-dimethoxyethane (10 ml). When evolution of gas ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.67 g) was added and the reaction mixture was stirred for 45 minutes. 7% aqueous citric acid solution (10 ml) was added, the organic phase was separated and the aqueous layer was extracted with ethyl acetate (2×20 ml). The combined organic phases were washed with water (10 ml) and dried (MgSO4). Volatile material was removed by evaporation to give a gum which was triturated first with dichloromethane and then ether to give 5-dimethylamino-N-(6-chloro-5-methyl-3-pyridazinyl)-1-naphthalenesulphonamide (0.2 g), m.p. 110°-112° C.; 1H NMR (d6 -DMSO): 2.30 (s,3H), 2.8 (s,6H), 7.23 (d,1H), 7.52-7.7 (m,3H), 8.3-8.5 (m,3H); mass spectrum (+ve FAB, methanol/dichloromethane/NBA): 376 (M)+.

Workup

  1. customthe organic phase was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 ml)
  3. washThe combined organic phases were washed with water (10 ml)
  4. dry with materialdried (MgSO4)
  5. customVolatile material was removed by evaporation
  6. customto give a gum which
  7. customwas triturated first with dichloromethane

Sources & evidence

ORD record
ord-fdf0199b697647cf8c53011297640b6d
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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