Chloroform → HCID 178457957, compound

HRID 247370Notes

Reaction equation

HRID 247370 reaction equation
S(O)(O)(=O)=O.[N:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][NH:13][C:14]([NH2:16])=[NH:15].[OH-:17].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+].C(Cl)(Cl)[Cl:27]>C1COCC1.CC#N>[ClH:27].[ClH:27].[CH2:7]([NH:6][C:11]([NH:15][C:14]([NH:13][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][N:6]=1)=[NH:16])=[O:17])[CH2:8][CH3:9]

Participants

7

Reactant 4

HCID 6212Chloroform2×HCID 14798Sodium HydroxideHCID 24436Sodium Sulfate2×HCID 178512760HCID 178512760, compound

Product 1

HCID 178457957HCID 178457957, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-Pyridylmethyl)guanidine sulfate (13.15 g) and 10 ml of CHCl3 are added to a vigorously stirred solution of 50% aqueous NaOH (5.2 g) and THF (15 ml). The mixture is stirred at RT for 2 hours. A 5 gram portion of solid anhydrous Na2SO4 is added and the mixture is stirred at room temperature for an additional hour. 100 ml of CHCl3 and 50 ml of CH3CN are added to the vigorously stirred mixture followed by an additional 5 g portion of Na2SO4. A solution of N-propyl isocyanate (5.11 g) and 75 ml of THF is added dropwise to the mixture and stirred at RT overnight. The solvent is evaporated in vacuo and the dark residue is mixed with 200 ml of CHCl3, 100 ml of saturated aqueous sodium chloride and 50 ml of water. The organic layer is separated and the aqueous layer is washed with an additional 200 ml portion of CHCl3. The organic phases are combined, washed with 70 ml of aqueous sodium chloride containing 5 ml of 50% aqueous NaOH, dried, filtered and concentrated in vacuo. The concentrate is acidified with ethereal HCl and evaporated to dryness under reduced pressure. The residue is taken up in boiling methanol, treated with Darco G-60 and filtered. The filtrate is concentrated to approximately 200 ml on a hotplate and diluted with approximately 200 ml of acetonitrile with continued heating. The hot solution is allowed to cool and the resultant precipitate collected, washed with acetonitrile and absolute ethanol. The solid is suspended in 200 ml of warm absolute ethanol, filtered while hot and dried in vacuo at 55° C. overnight to give 6.90 g of a blue white solid, MP 216°-218° w/dec.

Workup

  1. stirringthe mixture is stirred at room temperature for an additional hour
  2. stirringstirred at RT overnight
  3. customThe solvent is evaporated in vacuo
  4. additionthe dark residue is mixed with 200 ml of CHCl3, 100 ml of saturated aqueous sodium chloride and 50 ml of water
  5. customThe organic layer is separated
  6. washthe aqueous layer is washed with an additional 200 ml portion of CHCl3
  7. washwashed with 70 ml of aqueous sodium chloride containing 5 ml of 50% aqueous NaOH
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customevaporated to dryness under reduced pressure
  12. additiontreated with Darco
  13. filtrationand filtered
  14. concentrationThe filtrate is concentrated to approximately 200 ml on a hotplate
  15. additiondiluted with approximately 200 ml of acetonitrile with continued heating
  16. temperatureto cool
  17. customthe resultant precipitate collected
  18. washwashed with acetonitrile and absolute ethanol
  19. filtrationfiltered while hot and
  20. customdried in vacuo at 55° C. overnight

Sources & evidence

ORD record
ord-14d2e7f44da948bda5c08e146fc95117
Source dataset
uspto-grants-1987_11
Patent number
US04707478

Reaction notes

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