Ethyl 2-chloroacetoacetate → HCID 14500742, compound

HRID 1761558Notes

Reaction equation

HRID 1761558 reaction equation
[N:1]1([C:7]([NH:9][NH2:10])=S)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:11][CH:12]([C:18]([CH3:20])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[ClH:11].[CH3:20][C:18]1[NH:10][N:9]=[C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 4860905morpholine-4-carbothiohydrazide

Product 1

HCID 14500742HCID 14500742, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred slurry of 6.3 g (0.039 mole) of 4-morpholinecarbothioic acid hydrazide in 75 mL of absolute ethanol under nitrogen atmosphere was treated with 6.43 g (0.039 mole) of ethyl 2-chloroacetoacetate and the exothermic reaction mixture stirred at ambient temperature for 18 hr. The major portion of reaction mixture solids were dissolved by heating to reflux, the sulfur residue removed by filtration and the filtrate concentrated in vacuo to a solid, which was crystallized from 2-propyl alcohol to yield 5.5 g of white crystalline needles, mp 165°-173° C., as the hydrochloride salt.

Workup

  1. customThe major portion of reaction mixture solids
  2. dissolutionwere dissolved
  3. temperatureby heating
  4. temperatureto reflux
  5. customthe sulfur residue removed by filtration
  6. concentrationthe filtrate concentrated in vacuo to a solid, which
  7. customwas crystallized from 2-propyl alcohol

Sources & evidence

ORD record
ord-d9a4da3eacb24090900e54afef2db407
Source dataset
uspto-grants-1989_05
Patent number
US04826866

Reaction notes

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