Hydrochloric Acid → HCID 14500681, compound

HRID 1761537Notes

Reaction equation

HRID 1761537 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10](=S)[NH:11][NH2:12].Cl[CH:15]([C:21]([CH3:23])=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17].Cl>C(O)C>[CH3:23][C:21]1[NH:12][N:11]=[C:10]([NH:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 7369924-(2-Methoxyphenyl)-3-thiosemicarbazide

Product 1

HCID 14500681HCID 14500681, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 10.0 g (0.0507 mole) of 4-(2-methoxyphenyl)-3-thiosemicarbazide and 8.35 g (0.0507 mole) of ethyl 2-chloroacetoacetate in 150 mL of absolute ethanol was stirred for ~16 hr at room temperature. Alcoholic hydrogen chloride (2N, 50 mL) was added, the mixture heated at reflux for 1.0 hr, and the solution filtered while hot to remove precipitated sulfur. The filtrate was evaporated under reduced pressure, and the residue dissolved in hot ethanol, treated with charcoal and filtered through Celite®. The solution deposited 10.0 g of product, mp 162°-172° C. A similar recrystallization from absolute ethanol left 8.1 g, mp 155°-175° C. This product was dissolved in absolute ethanol, treated with charcoal, and filtered through Celite® 3 times. The filtrate deposited 4.3 g of product while standing for ~16 hr, mp 155.5°-159° C. which was a mixture of free base and hydrochloride salt. This last filtrate was left open to the atmosphere, and after approximately 50% of the solvent had evaporated, a solid precipitated and was collected by filtration: 1.4 g, mp 184°-191° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.0 hr
  3. filtrationthe solution filtered while hot
  4. customto remove
  5. customprecipitated sulfur
  6. customThe filtrate was evaporated under reduced pressure
  7. dissolutionthe residue dissolved in hot ethanol
  8. additiontreated with charcoal
  9. filtrationfiltered through Celite®
  10. customA similar recrystallization from absolute ethanol
  11. waitleft 8.1 g, mp 155°-175° C
  12. dissolutionThis product was dissolved in absolute ethanol
  13. additiontreated with charcoal
  14. filtrationfiltered through Celite® 3 times
  15. waitwhile standing for ~16 hr
  16. additiona mixture of free base and hydrochloride salt
  17. waitThis last filtrate was left open to the atmosphere
  18. customafter approximately 50% of the solvent had evaporated
  19. customa solid precipitated
  20. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7b6326a935bf4af2b93dd0602cadb573
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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