Carbon Disulfide → HCID 11302598, compound

HRID 2211177Notes

Reaction equation

HRID 2211177 reaction equation
[OH-].[K+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([NH:21][NH2:22])=[O:20].[C:23](=S)=[S:24]>CO>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]1[O:20][C:23](=[S:24])[NH:22][N:21]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 11141417HCID 11141417, compound

Product 1

HCID 11302598HCID 11302598, compoundYield 69.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium hydroxide (363.0 mg, 5.50 mmol) is added to a 0° C. suspension of 2-[(2,6-dichlorophenyl)amino]benzeneacetic acid, hydrazide (1.556 g, 5.01 mmol) and carbon disulfide (700 μl, 11.87 mmol) in 30 ml of methanol. The mixture is heated at reflux overnight under an atmosphere of nitrogen. The solution is concentrated in vacuo and the residue dissolved in water. The resulting aqueous solution is acidified with 1N hydrochloric acid and the resulting solids extracted into a 1:1 mixture of ether and ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is chromatographed, eluting with hexane:ethyl acetate (1:1), providing a white solid. Drying in vacuo at 65° C. for five days gives 1.22 g (65%) of product, mp 168°-170° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight under an atmosphere of nitrogen
  3. concentrationThe solution is concentrated in vacuo
  4. dissolutionthe residue dissolved in water
  5. extractionthe resulting solids extracted into a 1:1 mixture of ether and ethyl acetate
  6. dry with materialThe organic layer is dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed
  10. washeluting with hexane:ethyl acetate (1:1)
  11. customproviding a white solid
  12. customDrying in vacuo at 65° C. for five days

Sources & evidence

ORD record
ord-107338e27afa45d6ad6859b2668aadbe
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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