1,4-Dioxane → 2-(1-Methyl-1H-imidazol-4-yl)ethanamine bis(4-methylbenzenesulfonate)

HRID 1014962Notes

Reaction equation

HRID 1014962 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:12][N+:13]1[CH:21]=[C:20]2[N:15](C(=O)[NH:17][CH2:18][CH2:19]2)[CH:14]=1.O.[CH3:24][C:25]1[CH:30]=[CH:29][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.O1CCOCC1>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][CH:7]=1.[CH3:24][C:25]1[CH:26]=[CH:27][C:28]([S:31]([OH:34])(=[O:33])=[O:32])=[CH:29][CH:30]=1.[CH3:12][N:13]1[CH:21]=[C:20]([CH2:19][CH2:18][NH2:17])[N:15]=[CH:14]1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86622930HCID 86622930, compound

Product 1

HCID 862548242-(1-Methyl-1H-imidazol-4-yl)ethanamine bis(4-methylbenzenesulfonate)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-methyl-5-oxo-5,6,7,8-tetrahydroimidazo[1,5-c]pyrimidin-2-ium 4-methylbenzenesulfonate (625.1 g), 4-methylbenzenesulfonic acid hydrate (406.6 g), 1,4-dioxan (9.38 litres) and water (625 ml) was heated at reflux (ca. 90° C.) for 2.5 h. when the reaction was complete by nmr. The reaction mixture was concentrated by distillation at atmospheric pressure collecting 7.03 litres. The concentrate was allowed to cool to ca. 77° C., and IMS-G (1.56 litres) was added. The resulting bright solution was allowed to cool and was seeded with [2-(1-methyl-1H-imidazol-4-yl)ethyl]amine bis(4-methylbenzenesulfonate) (0.625 g) at ca. 54° C. The suspension was allowed to cool to ca. 22° C. and aged for 40 min. The solid was filtered off and washed successively with 1,4-dioxan-IMS (3:1, 1.25 litres), and then 1,4-dioxan (2×1.25 litres), pulled dry and dried in vacuo at ca. 50° C. to yield the title compound, 866.3 g.

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated by distillation at atmospheric pressure
  3. customcollecting 7.03 litres
  4. temperatureto cool to ca. 77° C.
  5. additionIMS-G (1.56 litres) was added
  6. temperatureto cool
  7. customwas seeded with [2-(1-methyl-1H-imidazol-4-yl)ethyl]amine bis(4-methylbenzenesulfonate) (0.625 g) at ca. 54° C
  8. temperatureto cool to ca. 22° C. and aged for 40 min
  9. filtrationThe solid was filtered off
  10. washwashed successively with 1,4-dioxan-IMS (3:1, 1.25 litres)
  11. dry with material1,4-dioxan (2×1.25 litres), pulled dry
  12. customdried in vacuo at ca. 50° C.

Sources & evidence

ORD record
ord-1ae5a96a6cf441db843f5f83e22e5071
Source dataset
uspto-grants-2011_07
Patent number
US07985740B2

Reaction notes

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