Hydrochloric Acid → HCID 14500681, compound

HRID 2350876Notes

Reaction equation

HRID 2350876 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 the 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 the precipitated sulfur
  5. customThe filtrate was evaporated under reduced pressure
  6. dissolutionthe residue dissolved in hot ethanol
  7. additiontreated with charcoal
  8. filtrationfiltered through Celite®
  9. customA similar recrystallization from absolute ethanol
  10. waitleft 8.1 g, mp 155°-175° C
  11. dissolutionThis product was dissolved in absolute ethanol
  12. additiontreated with charcoal
  13. filtrationfiltered through Celite® 3 times
  14. waitwhile standing for ~16 hr
  15. additiona mixture of free base and hydrochloride salt
  16. waitThis last filtrate was left open to the atmosphere
  17. customafter approximately 50% of the solvent had evaporated
  18. customa solid precipitated
  19. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-2c90b333406b44c2ad9031f47affdff3
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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