Carbon Disulfide → HCID 178527951, compound

HRID 329942Notes

Reaction equation

HRID 329942 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:11](=S)=[S:12].[OH-].[K+]>O.C(O)C>[SH:12][C:11]1[O:8][C:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)=[N:9][N:10]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 11112Nicotinic acid, hydrazideHCID 14797Potassium Hydroxide

Product 1

HCID 178527951HCID 178527951, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

13.7 g (0.1 mol) of nicotinic acid hydrazide and 8 g (0.105 mol) of carbon disulfide are added dropwise to a solution of 56 g (0.1 mol) of potassium hydroxide in 20 g of water and 350 ml of 95% ethanol. The reaction mixture is refluxed for 3 hours, then the solvent is evaporated off under vacuum and the residue is dried under a high vacuum. The dry residue is stirred in 75 ml of water, filtered, and the filtrate is neutralised with 1N hydrochloric acid. The precipitated product is isolated by filtration, washed in succession with acetone and hexane and vacuum dried, affording 9.9 g (55% of theory) of the title compound with a melting point of 237° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 3 hours
  2. customthe solvent is evaporated off under vacuum
  3. customthe residue is dried under a high vacuum
  4. filtrationfiltered
  5. customThe precipitated product is isolated by filtration
  6. washwashed in succession with acetone and hexane and vacuum
  7. customdried

Sources & evidence

ORD record
ord-4f9640a2824d436d87e2d4c6d5074c9c
Source dataset
uspto-grants-1990_01
Patent number
US04894380

Reaction notes

Loading…