Hydrochloric Acid → HCID 14500680, compound

HRID 1761536Notes

Reaction equation

HRID 1761536 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=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:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])[C:15]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 7362134-(2,6-Dimethylphenyl)-3-thiosemicarbazide

Product 1

HCID 14500680HCID 14500680, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.8 g (0.05 mole) of 4-(2,6-dimethylphenyl)-3-thiosemicarbazide and 8.48 g (0.05 mole) of ethyl 2-chloroacetoacetate (97%) in 75 mL of absolute ethanol was stirred under nitrogen atmosphere for one hour at room temperature. The reaction was slightly exothermic and the mixture changed from a white slurry to a yellow slurry as most of the solid dissolved. The mixture was treated with 40 mL of 2N ethanolic hydrogen chloride and allowed to stir at room temperature for 16 hr. The reaction mixture was heated at reflux for two hours; during this time it took on a dark orange color which cleared later as all the material dissolved (a small amount of insoluble material was also present). The reaction mixture was filtered and the solvent removed under reduced pressure leaving a yellow-orange solid. The solid was triturated with acetone which dissolved most of the orange color. Filtration gave 12.6 g of pale yellow crystals, mp 131°-137° C. Recrystallization of the yellow solid from acetone gave two crops of soft, fluffy, white product. Both crops were combined and analyzed, yield 8.5 g (62%), mp 142°-144° C.

Workup

  1. dissolutiondissolved
  2. stirringto stir at room temperature for 16 hr
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux for two hours
  5. dissolutiondissolved (a small amount of insoluble material
  6. filtrationThe reaction mixture was filtered
  7. customthe solvent removed under reduced pressure
  8. customleaving a yellow-orange solid
  9. customThe solid was triturated with acetone which
  10. dissolutiondissolved most of the orange color
  11. filtrationFiltration

Sources & evidence

ORD record
ord-0fbdc4f928a44f2f927e80b880be9616
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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