p-Toluenesulfonic acid → 2,3,4,6,7,8,9,10-Octahydropyrimido(1,2-a)azepinium (p-tolylsulphonate)

HRID 1892076Notes

Reaction equation

HRID 1892076 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH2:12]1[CH2:22][CH2:21][N:20]2[C:15](=[N:16][CH2:17][CH2:18][CH2:19]2)[CH2:14][CH2:13]1>CCOCC>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH2:12]1[CH2:22][CH2:21][N:20]2[C:15](=[N:16][CH2:17][CH2:18][CH2:19]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 162132142,3,4,6,7,8,9,10-Octahydropyrimido(1,2-a)azepinium (p-tolylsulphonate)

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A flame dried flask was charged with TsOH (1.0 g, 5.81 mmol), ether (20 mL) and a stirbar under dry nitrogen atmosphere. To the stirred solution, DBU (0.88 g, 5.81 mmol) was added. Instantly, a white precipitate formed and stirring was continued for 1 hour. The precipitate, 1.5 g (81%) of white salt, was then washed with excess ether and isolated by decantation. The salt was then dried under high vacuum.

Workup

  1. customA flame dried flask
  2. customInstantly, a white precipitate formed
  3. washThe precipitate, 1.5 g (81%) of white salt, was then washed with excess ether
  4. customisolated by decantation
  5. customThe salt was then dried under high vacuum

Sources & evidence

ORD record
ord-0edc7b4a7914457daabf3beb7bd3c6ef
Source dataset
uspto-grants-2013_08
Patent number
US08507640B2

Reaction notes

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