Ethyl 2-chloroacetoacetate → HCID 14500706, compound

HRID 1761549Notes

Reaction equation

HRID 1761549 reaction equation
[CH2:1]([NH:8][C:9](=S)[NH:10][NH2:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[Cl:13][CH:14]([C:20]([CH3:22])=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[ClH:13].[CH2:1]([NH:8][C:9]1[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:20]([CH3:22])[NH:11][N:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 12999905HCID 12999905, compound

Product 1

HCID 14500706HCID 14500706, compoundYield 30,856.301%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 30.3 g (0.16 mole) of 4-heptyl-3-thiosemicarbazide in 500 mL of absolute ethanol under nitrogen atmosphere was treated with the rapid addition of 26.3 g (0.16 mmole) of ethyl 2-chloroacetoacetate, stirred at ambient temperature for ~16 hr, heated at reflux for 3 hr and filtered hot. Concentration of the filtrate in vacuo gave a deep red oil. The oil solidified on standing for ~16 hr and was recrystallized from 2-propyl alcohol to give 15 g of fine white crystals, mp 83°-84° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hr
  3. filtrationfiltered hot
  4. customConcentration of the filtrate in vacuo gave a deep red oil
  5. waiton standing for ~16 hr
  6. customwas recrystallized from 2-propyl alcohol

Sources & evidence

ORD record
ord-dac4419e758c41dfbea8f714ecd8d8b3
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

Loading…