Triethylamine → HCID 35177757, compound

HRID 1025373Notes

Reaction equation

HRID 1025373 reaction equation
CS[C:3]([S:13][CH3:14])=[C:4]([C:10](=O)[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(O)C>[CH3:11][C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([S:13][CH3:14])[N:27]=[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4997384Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl esterHCID 12238987Benzenecarboximidamide, monoacetate

Product 1

HCID 35177757HCID 35177757, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2-(bis(methylthio)methylene)-3-oxobutanoate (500 mg, 2 mmol) in ethanol was added benzamidine acetate (732 mg, 6 mmol) and triethyl amine (1.41 mL) and the reaction mixture was refluxed overnight. The reaction mixture was concentrated and partitioned between ethyl acetate and water and the organic layer washed with water and dried over Na2SO4 and the solvent evaporated in vacuum. The crude product was purified by column chromatography over silica gel using 1% ethyl acetate in petroleum ether as eluent to give the desired product (350 mg). 1H-NMR 400 Hz (CDCl3): δ 8.50 (d, J=7.6 Hz, 2H), 7.50-7.46 (m, 3H), 4.45 (q, J=7.2 Hz, 2H), 2.67 (s, 3H), 2.65 (s, 3H), 1.44 (t, J=7.2 Hz, 3H); MS m/z 288.7 (M+1).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washthe organic layer washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent evaporated in vacuum
  7. customThe crude product was purified by column chromatography over silica gel using 1% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-7d40435bd1c542b9b649610072e6016d
Source dataset
uspto-grants-2014_05
Patent number
US08729079B2

Reaction notes

Loading…