2-Vinylpyridine → HCID 19045336, compound

HRID 1591147Notes

Reaction equation

HRID 1591147 reaction equation
O1C=CCCC1.[N+:7]([C:10]1[S:24][C:13]2[S:14][C:15]3([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:16][C:17](=[O:18])[C:12]=2[CH:11]=1)([O-:9])=[O:8].[CH:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1)=[CH2:26].O.O.O.C([O-])(=O)C.[Na+]>CO.O>[N+:7]([C:10]1[S:24][C:13]2[S:14][C:15]3([CH2:19][CH2:20][N:21]([CH2:26][CH2:25][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:22][CH2:23]3)[CH2:16][C:17](=[O:18])[C:12]=2[CH:11]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 75212-VinylpyridineHCID 23665404Sodium Acetate TrihydrateHCID 67724995HCID 67724995, compound

Product 1

HCID 19045336HCID 19045336, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution containing 660 mg (2.05 mmol) of 2'-Nitro-spiro(piperidine-4,6'-(6H)thieno[2,3-b]thiopyran)-4'(5'H)-one dihydropyran, 430 mg (4.1 mmol) of 2-vinylpyridine and 557 mg (4.1 mmol) of sodium acetate trihydrate in 10 ml of 1:1 methanol/water was heated at reflux for 4 hours. The reaction was cooled to room temperature and a solid separated. The solid was collected and dissolved in methanol and treated with excess ethanolic HCl. The dihydro chloride separated and was collected and dried over night in vacuo to give 482 mg of the product.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customa solid separated
  4. customThe solid was collected
  5. dissolutiondissolved in methanol
  6. additiontreated with excess ethanolic HCl
  7. customThe dihydro chloride separated
  8. customwas collected
  9. customdried over night in vacuo

Sources & evidence

ORD record
ord-f5f193f0febf4d70996f1cc668dfbb59
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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