Acetic Acid → Methyl 3-carbamimidoylbenzoate acetate

HRID 330795Notes

Reaction equation

HRID 330795 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].O.CC1O[N:10]=[C:9]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])[N:8]=1>CO>[C:1]([OH:4])(=[O:3])[CH3:2].[C:9]([C:12]1[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=1)[C:15]([O:17][CH3:18])=[O:16])(=[NH:8])[NH2:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962Water2×HCID 53429639Methyl 3-(5-methyl-1,2,4-oxadiazol-3-YL)benzoate

Product 1

HCID 66985510Methyl 3-carbamimidoylbenzoate acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

150 ml of acetic acid, 150 ml of water and 50 g of water-moist Raney nickel are added to a solution of 327 g (1.47 mol) of methyl 3-(5-methyl-1,2,4-oxadiazol-3-yl)benzoate in 3 l of methanol, and the mixture is hydrogenated at room temperature and atmospheric pressure for 18 hours. The catalyst is filtered off, and the filtrate is evaporated. The residue is taken up in tert-butyl methyl ether, heated to the boil and filtered off with suction. The residue is dried in vacuo: 3-methoxycarbonylbenzamidinium acetate as colourless crystals; m.p. 222°; ESI 179 (M+H); HPLC: Rt.=1.40 min (method A).

Workup

  1. customis hydrogenated at room temperature
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. temperatureheated to the boil
  5. filtrationfiltered off with suction
  6. customThe residue is dried in vacuo
  7. custom=1.40 min (method A)

Sources & evidence

ORD record
ord-4b207866bef24aa2bdebbf6b53031d8c
Source dataset
uspto-grants-2014_11
Patent number
US08877751B2

Reaction notes

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