Ethyl 2-chloroacetoacetate → HCID 14500740, compound

HRID 2350897Notes

Reaction equation

HRID 2350897 reaction equation
[CH2:1]([N:5]([CH2:10][CH2:11][CH2:12][CH3:13])[C:6](=S)[NH:7][NH2:8])[CH2:2][CH2:3][CH3:4].[Cl:14][CH:15]([C:21]([CH3:23])=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[ClH:14].[CH2:1]([N:5]([CH2:10][CH2:11][CH2:12][CH3:13])[C:6]1[C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:21]([CH3:23])[NH:8][N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 11858Ethyl 2-chloroacetoacetateHCID 12236601HCID 12236601, compound

Product 1

HCID 14500740HCID 14500740, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A stirred solution of 14.3 g (0.07 mole) of 4,4-di-n-butyl-3-thiosemicarbazide in 100 mL of absolute ethanol was cooled to 10° C. under nitrogen atmosphere, treated with 11.6 g (0.07 mole) of ethyl 2-choroacetoacetate, warmed to 60° C., then cooled to ambient temperature and stirred for 18 hr. The reaction mixture was heated to reflux in order to dissolve the precipitate, filtered to remove amorphous sulfur and concentrated in vacuo to give a solid. The solid was recrystallized from acetone to yield 8 g of white crystalline product, mp 159°-162° C., as the hydrochloride salt.

Workup

  1. temperaturecooled to ambient temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux in order
  4. dissolutionto dissolve the precipitate
  5. filtrationfiltered
  6. customto remove amorphous sulfur
  7. concentrationconcentrated in vacuo
  8. customto give a solid
  9. customThe solid was recrystallized from acetone

Sources & evidence

ORD record
ord-95dbcabb25464cb090796e0ded972e0d
Source dataset
uspto-grants-1989_10
Patent number
US04871737

Reaction notes

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