Sodium ethoxide → HCID 178470798, compound

HRID 606446Notes

Reaction equation

HRID 606446 reaction equation
[NH2:1][C:2]([NH:4][NH:5][C:6](=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[S:3].[O-]CC.[Na+]>C(O)C>[SH:3][C:2]1[NH:4][N:5]=[C:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:1]=1

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 57708832Ethyl 3-[2-(aminocarbonothioyl)hydrazino]-3-oxopropanoate

Product 1

HCID 178470798HCID 178470798, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of ethyl 3-[2-(aminocarbonothioyl)hydrazino]-3-oxopropanoate (14.0 g, 68.2 mmol) and sodium ethoxide (9.52 g, 140 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 an orange powder (12.2 g, 96%).

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-1545db3bcd9e4b34940f1454171f0982
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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