Sodium ethoxide → HCID 178471187, compound

HRID 606453Notes

Reaction equation

HRID 606453 reaction equation
[NH2:1][C:2]([NH:4][NH:5][C:6](=O)[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[S:3].[O-]CC.[Na+]>C(O)C>[SH:3][C:2]1[NH:4][N:5]=[C:6]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:1]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 22930781Ethyl 4-[2-(aminocarbothioyl)hydrazino]-4-oxobutanoate

Product 1

HCID 178471187HCID 178471187, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of ethyl 4-[2-(aminocarbonothioyl)hydrazino]-4-oxobutanoate (16.8 g, 76.7 mmol) and sodium ethoxide (10.4 g, 153 mmol) in ethanol (200 mL) was stirred at 80° C. for 15 hr. The mixture was concentrated under reduced pressure, and the residue was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated to give the title compound as a white powder (14.0 g, 91%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d4573363600c43dc98df15b1b70f17a3
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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