6-Amino-3-chloropyridazine → 2-phenyl-N-(6-chloro-3-pyridazinyl)benzenesulphonamide

HRID 2287374Notes

Reaction equation

HRID 2287374 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:2]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:4]=[CH:5][CH:6]=1.[NH2:17][C:18]1[N:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=1>N1C=CC=CC=1>[C:11]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=2[S:7]([NH:17][C:18]2[N:19]=[N:20][C:21]([Cl:24])=[CH:22][CH:23]=2)(=[O:9])=[O:8])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 216436-Amino-3-chloropyridazineHCID 27566802-Phenylbenzene-1-sulfonyl chloride

Product 1

HCID 98845952-phenyl-N-(6-chloro-3-pyridazinyl)benzenesulphonamideYield 18.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-biphenylsulphonyl chloride (0.31 g), 3-amino-6-chloropyridazine (0.5 g) in pyridine (5 ml) was stirred for 18 hours. Volatile material was removed by evaporation and 1M sodium hydroxide solution (4 ml) and methanol (10 ml) were added. The reaction mixture was stirred on a steam bath for 20 minutes and, after cooling, volatile material was again removed by evaporation. The residue was dissolved in water (100 ml) and acidified with concentrated hydrochloric acid to pH 1-2 and extracted with ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and evaporated to give a solid. The solid was recrystallised twice from isopropanol to give 2-phenyl-N-(6-chloro-3-pyridazinyl)benzenesulphonamide (0.08 g), m.p. 196-198° C.; mass spectrum (+ve FAB, methanol/dichloromethane/NBA): 346 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation and 1M sodium hydroxide solution (4 ml) and methanol (10 ml)
  2. additionwere added
  3. temperatureafter cooling
  4. customvolatile material was again removed by evaporation
  5. dissolutionThe residue was dissolved in water (100 ml)
  6. extractionextracted with ethyl acetate (3×50 ml)
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. customevaporated
  9. customto give a solid
  10. customThe solid was recrystallised twice from isopropanol

Sources & evidence

ORD record
ord-851898b1fa7543c48450a76ed2128f5b
Source dataset
uspto-grants-2000_07
Patent number
US06083951

Reaction notes

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