Methanesulfonic Acid → Methanesulfonate

HRID 66162Notes

Reaction equation

HRID 66162 reaction equation
C(O[C:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5][C:6]1[CH2:10][CH2:9][CH2:8][N:7]=1)C.F[B-](F)(F)F.[CH3:22][S:23]([OH:26])(=[O:25])=[O:24]>C(NCC)C>[CH2:6]([N:7]([CH2:8][CH3:9])[C:4]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[CH:5][C:6]1[CH2:10][CH2:9][CH2:8][N:7]=1)[CH3:5].[CH3:22][S:23]([O-:26])(=[O:25])=[O:24]

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 867362142-(2-Ethoxy-2-phenyl-ethenyl)-1-pyrroline tetrafluoroborate

Product 2

HCID 85257MethanesulfonateHCID 541301342-[2-(Diethylamino)-2-phenyl-ethenyl]-1-pyrroline-

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

The solution of 9.1 g (0.03 mole) of 2-[2-ethoxy-2-phenyl-ethenyl]-1-pyrroline-tetrafluoroborate in 25 ml of diethylamine is refluxed for 12 hours; it is then processed analogously to Example 1 to yield crude 2-[2-(diethylamino)-2-phenyl-ethenyl]-1-pyrroline. By the addition of 2.8 g of methanesulphonic acid to the solution of the crude base in isopropanol, removal of the crystals by filtration and recrystallisation from isopropanol, there is obtained 2-[2-(diethylamino)-2-phenyl-ethenyl]-1-pyrroline-(1:1)-methanesulphonate, m.p. 143°-145° (decomposition).

Workup

  1. customto yield crude 2-[2-(diethylamino)-2-phenyl-ethenyl]-1-pyrroline
  2. customto the solution of the crude base in isopropanol, removal of the crystals
  3. filtrationby filtration and recrystallisation from isopropanol

Sources & evidence

ORD record
ord-e315eb8df3d443d399f831a2d7ea1a79
Source dataset
uspto-grants-1978_12
Patent number
US04130652

Reaction notes

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