Ethyl 2-chloroacetoacetate → HCID 131716144, compound

HRID 2350902Notes

Reaction equation

HRID 2350902 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10](=S)[NH:11][NH2:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:14][CH:15]([C:21]([CH3:23])=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>Cl.C(O)C>[ClH:14].[CH2:19]([O:18][C:16]([C:15]1[C:10]([NH:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:11][NH:12][C:21]=1[CH3:23])=[O:17])[CH3:20]

Participants

5

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 2760462N-[2-(Piperidin-1-yl)ethyl]hydrazinecarbothioamide

Product 1

HCID 131716144HCID 131716144, compoundYield 55.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A stirred solution of 6 g (0.03 mole) of 4-(2-piperidinoethyl)-3-thiosemicarbazide in 30 mL of 2N ethanolic hydrogen chloride was diluted to 60 mL with absolute ethanol, treated with 4.9 g (0.03 mole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for 3 hr, and heated at reflux for 2 hr. The reaction mixture was filtered hot to remove amorphous sulfur and the filtrate concentrated to an orange oil. Trituration with refluxing 2-propyl ether and cooling gave a plastic mass with crystals. The 2-propyl ether was decanted and the residual material recrystallized from 2-propyl alcohol/2-propyl ether to give 8 g of crude product. A second recrystallization from 2-propyl alcohol/2-propyl ether gave 5.3 g of beige crystalline product, mp 198°-200° C. as the dihydrochloride salt.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hr
  3. filtrationThe reaction mixture was filtered hot
  4. customto remove amorphous sulfur
  5. concentrationthe filtrate concentrated to an orange oil
  6. temperatureTrituration with refluxing 2-propyl ether and cooling
  7. customgave a plastic mass with crystals
  8. customThe 2-propyl ether was decanted
  9. customthe residual material recrystallized from 2-propyl alcohol/2-propyl ether
  10. customto give 8 g of crude product
  11. customA second recrystallization from 2-propyl alcohol/2-propyl ether

Sources & evidence

ORD record
ord-ddb1f1ab06614ebfa524bc240a84fa6b
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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