Acetic Acid → HCID 57893425, compound

HRID 2046248Notes

Reaction equation

HRID 2046248 reaction equation
C(O[C:4](=[O:22])[C:5](=[N:12][NH:13][C:14](=[O:21])[CH2:15][C:16]([O:18]CC)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)C.[NH:23](C(=O)CC(OCC)=O)N.[C:33]([C:41]([O:43]CC)=[O:42])(=O)C1C=CC=CC=1.C(O)(=O)C.S([O-])([O-])(=O)=O.[Mg+2]>ClCCl>[OH:22][C:4]1[C:5]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[N:12][NH:13][C:14](=[O:21])[C:15]=1[C:16]([NH:23][CH2:33][C:41]([OH:43])=[O:42])=[O:18]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 15349Ethyl benzoylformateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 252897Ethyl 3-hydrazino-3-oxopropionateHCID 86623016HCID 86623016, compound

Product 1

HCID 57893425HCID 57893425, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 3-{2-[2-(ethyloxy)-2-oxo-1-phenylethylidene]hydrazino}-3-oxopropanoate. A mixture of ethyl 3-hydrazino-3-oxopropionate (1.46 g, 10.0 mmol), ethyl benzoylformate (2.14 g, 12.0 mmol), acetic acid (0.5 mL, 8.3 mmol) and dichloromethane (10 mL) was stirred at room temperature with excess anhydrous magnesium sulfate for 20 h, then filtered and the cake washed with ethyl acetate. The filtrate was evaporated under reduced pressure, azeotroped 3 times with toluene and chromatographed (silica gel, 10-3-% ethyl acetate/hexane) to give the title compound (0.773 g, 25%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.15 (t, J=7.07 Hz, 3H) 1.30 (t, J=7.07 Hz, 3H) 3.74 (s, 2H) 4.08 (q, J=7.07 Hz, 2H) 4.40 (q, J=7.18 Hz, 2H) 7.42-7.49 (m, 3H) 7.55-7.59 (m, 2H) 11.57 (s, 1H).

Workup

  1. filtrationfiltered
  2. washthe cake washed with ethyl acetate
  3. customThe filtrate was evaporated under reduced pressure
  4. customazeotroped 3 times with toluene
  5. customchromatographed (silica gel, 10-3-% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-99f935609f5748dfa09e31bf3c496ea8
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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