Acetic Acid → HCID 86745031, compound

HRID 728037Notes

Reaction equation

HRID 728037 reaction equation
C(O)(=O)C.[CH:5]([NH:7][CH2:8][CH2:9][S:10][CH2:11][C:12](=O)[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:6].[NH3:20]>CO>[NH2:20]/[C:12](/[CH2:11][S:10][CH2:9][CH2:8][NH:7][CH:5]=[O:6])=[CH:13]\[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 19823379HCID 19823379, compound

Product 1

HCID 86745031HCID 86745031, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Acetic acid is added to a solution of ethyl 4-(2-formylamino-ethylthio)-3-oxo-butanoate (12.5 g) in MeOH (ml 120), previously saturated with ammonia at 0° C. and cooled at 0° C., up to pH 4-45. The mixture is refluxed for 2 hours and the excess solvent is evaporated in vacuum, to give a syrup from which a solid material is separated by treatment with AcOEt. After filtration, the organic phase is washed with water (8×10 ml), and with a saturated aqueous solution of NaHCO3 (3×10 ml), dried (Na2SO4) and concentrated in vacuum to give 11,5 g of ethyl 3-amino-4-(2-formylaminoethylthio)crotonate as a yellow oil.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. customthe excess solvent is evaporated in vacuum
  3. customto give a syrup from which a solid material
  4. customis separated by treatment with AcOEt
  5. filtrationAfter filtration
  6. washthe organic phase is washed with water (8×10 ml)
  7. dry with materialwith a saturated aqueous solution of NaHCO3 (3×10 ml), dried (Na2SO4)
  8. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-a15a9f55509149ffa5080d6ad5072059
Source dataset
uspto-grants-1991_09
Patent number
US05047414

Reaction notes

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