Acetic Anhydride → 2-(4-Isobutylphenyl)propionamidine acetate salt

HRID 2242925Notes

Reaction equation

HRID 2242925 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:16])[C:12]([NH:14]O)=[NH:13])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[C:17]([O:20]C(=O)C)(=[O:19])[CH3:18]>C(O)(=O)C.[Pd]>[C:17]([OH:20])(=[O:19])[CH3:18].[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH3:16])[C:12]([NH2:14])=[NH:13])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178440852HCID 178440852, compound

Product 1

HCID 673682322-(4-Isobutylphenyl)propionamidine acetate saltYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2-(4-isobutylphenyl)-N-hydroxy-propionamidine (0.097 g, 0.44 mmol) is dissolved in acetic acid (3 mL) and treated at r.t. with acetic anhydride (0.06 mL, 0.66 mmol). 10% Pd on activated charcoal (0.03 g) is added and H2 is bubbled into the flask until the complete disappearance of the starting reagent. Methyl alcohol (5 mL) is added, the catalyst filtered off on a Celite cake and the solvents evaporated under reduced pressure to give an oily residue. Crystallisation of the crude residue from n-hexane gives 2-(4-isobutylphenyl)propionamidine acetate salt as white solid (0.106 g, 0.4 mmol). Yield 91%. m.p. >220° C. 1H-NMR (DMSO-d6): δ 8.70-8.50 (bs, NH3++NH); 7.42 (d, 2H, J=7 Hz); 7.23 (d, 2H, J=7 Hz); 3.85 (q, 1H, J=8 Hz); 2.52 (d, 2H, J=8 Hz); 1.97 (m, 1H); 1.75 (s, 3H); 1.60 (d, 3H, J=8 Hz); 0.95 (d, 6H, J=8 Hz).

Workup

  1. customH2 is bubbled into the flask until the complete disappearance of the starting reagent
  2. additionMethyl alcohol (5 mL) is added
  3. filtrationthe catalyst filtered off on a Celite cake
  4. customthe solvents evaporated under reduced pressure
  5. customto give an oily residue
  6. customCrystallisation of the crude residue from n-hexane

Sources & evidence

ORD record
ord-10592229c050423fa7b97a9abfed393f
Source dataset
uspto-grants-2010_03
Patent number
US07674806B2

Reaction notes

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