Hydrochloric Acid → HCID 19009010, compound

HRID 1742281Notes

Reaction equation

HRID 1742281 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[N:14]=[N:13][C:12]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-].[NH2:25][N+:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[OH-].[Na+].Cl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(Cl)Cl.O>[C:18]1([S:15]([C:12]2[N:13]=[N:14][C:9]([C:8]3[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:25][N:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=34)=[CH:10][CH:11]=2)(=[O:17])=[O:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 11232442HCID 11232442, compound

Product 1

HCID 19009010HCID 19009010, compoundYield 69.3%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A two-phase mixture of 6-(2-phenylethynyl)-3-phenylsulfonylpyridazine (23.3 g), 1-aminopyridinium iodide (90%; 26.9 g), sodium hydroxide (11.6 g), and benzyltrimethylammonium chloride (1.35 g) in a mixture of methylene chloride (233 ml) and water (233 ml) was stirred for 2 hours at room temperature. Water (233 ml) was added to the reaction mixture, and the mixture was acidified with 36% hydrochloric acid (20 ml). The organic layer was separated, washed twice with water and once with sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was washed with hot ethanol (300 ml) to give 3-(3-phenylsulfonylpyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (20.8 g). An analytical sample was prepared by recrystallization from ethyl acetate.

Workup

  1. customThe organic layer was separated
  2. washwashed twice with water and once with sodium chloride aqueous solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was washed with hot ethanol (300 ml)

Sources & evidence

ORD record
ord-0c8a0588fd6e4eed8ec470d9cebfc312
Source dataset
uspto-grants-1994_08
Patent number
US05338743

Reaction notes

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