Carbon Disulfide → HCID 43831517, compound

HRID 1943930Notes

Reaction equation

HRID 1943930 reaction equation
[OH-].[Na+:2].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].[C:11](=[S:13])=[S:12]>O.CCO>[C:3]([C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:11]([S-:13])[S-:12])#[N:4].[Na+:2].[Na+:2]

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 7764Ethyl cyanoacetateHCID 14798Sodium Hydroxide

Product 1

HCID 43831517HCID 43831517, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of NaOH (40 g, 999 mmol) in H2O (40 mL) was slowly added via an addition funnel such that the internal temperature did not exceed 10° C. to a cold (0° C.) solution of ethyl 2-cyanoacetate (53.3 mL, 499.5 mmol) and carbon disulfide (30.2 mL, 499.5 mmol) in absolute EtOH (600 mL) Once the addition was complete, the reaction mixture was allowed to stir at room temperature for 10 minutes. The reaction mixture was then cooled to 5° C. The resulting solids were isolated by filtration and washed with EtOH (100 mL), ether (500 mL) and dried in vacuo to give sodium 2-cyano-3-ethoxy-3-oxoprop-1-ene-1,1-bis(thiolate) (110.0 g, 97%) as a solid.

Workup

  1. temperatureThe reaction mixture was then cooled to 5° C
  2. customThe resulting solids were isolated by filtration
  3. washwashed with EtOH (100 mL), ether (500 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-caa81b2a25ef454e960941c10b4d5aac
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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