Methanesulfonic Acid → HCID 11322135, compound

HRID 1595037Notes

Reaction equation

HRID 1595037 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]#[N:10])=[CH:5][CH:4]=1)#[N:2].[H][H].[CH3:13][S:14]([OH:17])(=[O:16])=[O:15]>[Pd].C(O)(C)C>[CH3:13][S:14]([O-:17])(=[O:16])=[O:15].[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH3+:10])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 121721,4-DicyanobenzeneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11322135HCID 11322135, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

1,4-Dicyanobenzene (2.0 g; 15.6 mmol) and palladium on activated carbon (1.0 mol % Pd/1,4-dicyanobenzene) were suspended in iso-propanol (30 mL) at 50° C. Hydrogen was continuously added at a pressure of 6 atm. When the desired conversion was obtained (2.5 h), the hydrogen was replaced by nitrogen and the solid material (Pd/C and unreacted 1,4-dicyanobenzene) was filtered off. Methanesulphonic acid (1.5 g; 15.6 mmol) was added to the clear solution. The crystals which formed were centrifuged, washed with a small amount iso-propanol and dried to yield 2.77 g (79%) of 4-cyanobenzylammonium methanesulphonate with a HPLC purity of 91.2 ae %.

Workup

  1. customWhen the desired conversion was obtained (2.5 h)
  2. filtrationthe solid material (Pd/C and unreacted 1,4-dicyanobenzene) was filtered off
  3. customThe crystals which formed
  4. washwashed with a small amount iso-propanol
  5. customdried

Sources & evidence

ORD record
ord-70ca69de06854398b727fb399e4e7944
Source dataset
uspto-grants-2001_09
Patent number
US06284913B1

Reaction notes

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