Hydrochloric Acid → HCID 70377880, compound

HRID 1761561Notes

Reaction equation

HRID 1761561 reaction equation
[CH3:1][N:2]([CH3:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=S)[NH:8][NH2:9].Cl.[Cl:13][CH:14]([C:20]([CH3:22])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[ClH:13].[CH2:18]([O:17][C:15]([C:14]1[C:7]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:11])[CH3:1])=[N:8][NH:9][C:20]=1[CH3:22])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11858Ethyl 2-chloroacetoacetateHCID 10012455HCID 10012455, compound

Product 1

HCID 70377880HCID 70377880, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 7.05 g (0.04 mole) of 4-(3-dimethylaminopropyl)-3-thiosemicarbazide in 50 mL of absolute ethanol under nitrogen atmosphere was treated with 40 mL of 2N ethanolic hydrogen chloride and then with 6.6 g (0.04 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 2 hr and heated at reflux for 5 hr. The reaction mixture was filtered hot to remove some crystalline sulfur and the filtrate solidified on cooling to give 8.3 g of crude product. After 5 recrystallizations from methyl ethyl ketone/methanol with charcoal treatment of the final recrystallization, a crystalline product was obtained, 3.4 g, mp 195°-196° C. After drying at 82° C. under reduced pressure, it was submitted for elemental analysis.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hr
  3. filtrationThe reaction mixture was filtered hot
  4. customto remove some crystalline sulfur
  5. temperatureon cooling

Sources & evidence

ORD record
ord-92019a3ea0ac412a819155dbe6d9454f
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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