Ethyl Acetate → HCID 13885857, compound

HRID 1722392Notes

Reaction equation

HRID 1722392 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:16](=O)[CH3:17])[C:12]([O:14][CH3:15])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl.[CH3:20][O:21][C:22]1[CH:32]=[CH:31][C:25]([CH2:26][S:27][C:28](=[NH:30])[NH2:29])=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][S:27][C:28]2[NH:30][C:16]([CH3:17])=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[N:29]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 517045Sodium AcetateHCID 1536427Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoateHCID 13885856(4-Methoxyphenyl)methyl carbamimidothioate--hydrogen chloride (1/1)

Product 1

HCID 13885857HCID 13885857, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, methyl ester (5.0 g, 0.02 mole) in 20 ml of dimethylformamide under argon at room temperature was treated with S-(4-methoxybenzyl)thiopseudourea, hydrochloride (4.65 g, 0.02 mole) and sodium acetate (1.64 g, 0.02 mole). The mixture was then heated at 65±5° C. for 3 hours. Upon cooling, ethyl acetate was added and a small amount of solids were filtered. The filtrate was washed with water (twice), aqueous sodium bicarbonate and saturated brine. The aqueous washes were extracted with fresh ethyl acetate. The combined filtrate and washings were dried (magnesium sulfate) and concentrated in vacuo to give about 9 g of crude product. Crystallization from acetone-isopropyl ether gave 6.8 g of product, melting point 125°-127.5° C., tlc, silica gel, ethyl acetate/hexane (1:1), Rf =0.48.

Workup

  1. temperatureUpon cooling
  2. filtrationa small amount of solids were filtered
  3. washThe filtrate was washed with water (twice), aqueous sodium bicarbonate and saturated brine
  4. extractionThe aqueous washes were extracted with fresh ethyl acetate
  5. dry with materialThe combined filtrate and washings were dried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. customto give about 9 g of crude product
  8. customCrystallization from acetone-isopropyl ether

Sources & evidence

ORD record
ord-21144a38546d4933943783fb29ce70ae
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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